Methods for producing triflazoles or related derivatives thereof, and the resulting products are provided. For example, triflazoles can be prepared by reaction of trifluoromethanesulfonyl fluoride with an azole or azolate salt. Yields up to 78% are obtained. Triflazoles can be prepared by the reaction of a trifluoromethanesulfonyl fluoride with an N-silylazole in the presence of a basic catalyst. Yields up to 97% are obtained.
C07D 233/60 - Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
Methods for producing triflazoles or related derivatives thereof, and the resulting products are provided. For example, triflazoles can be prepared by reaction of trifluoromethanesulfonyl fluoride with an azole or azolate salt. Yields up to 78% are obtained. Triflazoles can be prepared by the reaction of a trifluoromethanesulfonyl fluoride with an N-silylazole in the presence of a basic catalyst. Yields up to 97% are obtained.
C07D 231/12 - Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
C07D 233/60 - Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
Methods for producing triflazoles or related derivatives thereof, and the resulting products are provided. For example, triflazoles can be prepared by reaction of trifluoromethanesulfonyl fluoride with an azole or azolate salt. Yields up to 78% are obtained. Triflazoles can be prepared by the reaction of a trifluoromethanesulfonyl fluoride with an N-silylazole in the presence of a basic catalyst. Yields up to 97% are obtained.
C07D 233/60 - Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
C07D 231/12 - Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
4.
Sulfonyldiazoles and N-(fluorosulfonyl)azoles, and methods of making the same
The present disclosure provides methods for producing N-(fluorosulfonyl)azoles, sulfonyldiazoles, or related derivatives thereof, and the related products including N-(fluorosulfonyl)azoles, sulfonyldiazoles, and related derivatives thereof. For example, an N-(fluorosulfonyl)azole is obtained by reaction of sulfuryl fluoride with an azoles, an azolate salt, an N-silylazole, or a combination thereof. Symmetric and asymmetric sulfonyldiazoles are obtained by further reaction of such an N-(fluorosulfonyl)azole with azoles, azolate salts, or N-silylazoles. A sulfonyldiazole can be also produced by reacting sulfuryl fluoride with an azole, an N-silylazole, or a combination thereof in one pot.
C07D 403/12 - Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group containing two hetero rings linked by a chain containing hetero atoms as chain links
C07D 231/24 - One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms having sulfone or sulfonic acid radicals in the molecule
5.
SULFONYLDIAZOLES AND N-(FLUOROSULFONYL)AZOLES, AND METHODS OF MAKING THE SAME
The present disclosure provides methods for producing N-(fluorosulfonyl)azoles, sulfonyldiazoles, or related derivatives thereof; and the related products including N- (fluorosulfonyl)azoles, sulfonyldiazoles, and related derivatives thereof. For example, an N- (fluorosulfonyl)azole is obtained by reaction of sulfuryl fluoride with an azoles, an azole anion compound, a silylazole, or a combination thereof. Symmetric and asymmetric sulfonyldiazoles are obtained by further reaction of such an N-(fluorosulfonyl)azole with azoles, azole anion compounds, or silylazoles. A sulfonyldiazole can be also produced by reacting sulfuryl fluoride with an azole, a silylazole, or a combination thereof in one pot.
The present disclosure provides methods for producing N-(fluorosulfonyl)azoles, sulfonyldiazoles, or related derivatives thereof; and the related products including N- (fluorosulfonyl)azoles, sulfonyldiazoles, and related derivatives thereof. For example, an N- (fluorosulfonyl)azole is obtained by reaction of sulfuryl fluoride with an azoles, an azole anion compound, a silylazole, or a combination thereof. Symmetric and asymmetric sulfonyldiazoles are obtained by further reaction of such an N-(fluorosulfonyl)azole with azoles, azole anion compounds, or silylazoles. A sulfonyldiazole can be also produced by reacting sulfuryl fluoride with an azole, a silylazole, or a combination thereof in one pot.
The present disclosure provides methods for producing N-(fluorosulfonyl)azoles, sulfonyldiazoles, or related derivatives thereof; and the related products including N-(fluorosulfonyl)azoles, sulfonyldiazoles, and related derivatives thereof. For example, an N-(fluorosulfonyl)azole is obtained by reaction of sulfuryl fluoride with an azoles, an azole anion compound, a silylazole, or a combination thereof. Symmetric and asymmetric sulfonyldiazoles are obtained by further reaction of such an N-(fluorosulfonyl)azole with azoles, azole anion compounds, or silylazoles. A sulfonyldiazole can be also produced by reacting sulfuryl fluoride with an azole, a silylazole, or a combination thereof in one pot.
C07D 233/58 - Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
C07D 235/06 - BenzimidazolesHydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
C07F 7/10 - Compounds having one or more C—Si linkages containing nitrogen
C07D 403/12 - Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group containing two hetero rings linked by a chain containing hetero atoms as chain links
C07C 303/34 - Preparation of esters or amides of sulfuric acidsPreparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfuric acids
11.
METHOD FOR MAKING N-(FLUOROSULFONYL) DIMETHYLAMINE
Dimethylamine (Me2NH) is reacted with sulfuryl fluoride (S02F2) to form at least a first phase comprising N-(fluorosulfonyl) dimethylamine (FS02NMe2), tetramethylsulfamide (S02(NMe2)2), or a combination thereof. A second phase, which may include dimethylamine hydrofluoride (Me2NH2F), may be also formed and separated from the first phase. FS02NMe2 or S02(NMe2)2 is then isolated from the first phase. For example, the first phase may be a liquid phase, and FS02NMe2 and S02(NMe2)2 are separated by distillation, optionally under reduced pressure.
C07C 303/34 - Preparation of esters or amides of sulfuric acidsPreparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfuric acids
C07C 303/34 - Preparation of esters or amides of sulfuric acidsPreparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfuric acids
13.
METHOD FOR MAKING N-(FLUOROSULFONYL) DIMETHYLAMINE
Dimethylamine (Me2NH) is reacted with sulfuryl fluoride (S02F2) to form at least a first phase comprising N-(fluorosulfonyl) dimethylamine (FS02NMe2), tetramethylsulfamide (S02(NMe2)2), or a combination thereof. A second phase, which may include dimethylamine hydrofluoride (Me2NH2F), may be also formed and separated from the first phase. FS02NMe2 or S02(NMe2)2 is then isolated from the first phase. For example, the first phase may be a liquid phase, and FS02NMe2 and S02(NMe2)2 are separated by distillation, optionally under reduced pressure.
C07C 303/34 - Preparation of esters or amides of sulfuric acidsPreparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfuric acids
C07C 307/06 - Diamides of sulfuric acids having nitrogen atoms of the sulfamide groups bound to acyclic carbon atoms
C07C 307/02 - Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids
14.
Synthesis of tetrabutylammonium bis(fluorosulfonyl)imide and related salts
The present invention is directed to methods comprising adding ammonia, either as an ammonium salt or as a gas at pressures below 0.01 MPa, to a sulfuryl fluoride solution to form the anion of bis(fluorosulfonyl)amine under conditions well suited for large-scale production. The bis(fluorosulfonyl)amine so produced can be isolated by methods described in the prior art, or isolated as an organic ion pair, such as an alkylammonium solid salt, or as an ionic liquid.
C07C 209/68 - Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
C07C 311/48 - Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
C01B 21/086 - Compounds containing nitrogen and non-metals containing one or more sulfur atoms
15.
Preparation of fluorosulfonate esters and onium salts derived therefrom
C07C 309/00 - Sulfonic acidsHalides, esters, or anhydrides thereof
C07C 209/00 - Preparation of compounds containing amino groups bound to a carbon skeleton
C07C 211/63 - Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
C07C 213/02 - Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
C07D 233/58 - Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
C07D 295/037 - Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements with quaternary ring nitrogen atoms
C01B 17/45 - Compounds containing sulfur and halogen, with or without oxygen
16.
PREPARATION OF FLUOROSULFONATE ESTERS AND ONIUM SALTS DERIVED THEREFROM
The present invention is directed to methods for preparing a fluorosulfonate ester or a salt thereof, through a reaction of a dissolved sulfonyl fluoride (RFSO2F) with alkoxide anion (RO- ) optionally in the presence of an aprotic base (B), where RF is fluorine or a C1-C8 perfluoroalkyl group, and R is a primary alkyl or alkoxyalkyl. Alkoxide anion (RO-) can be generated from a precursor such as an alcohol or silyl ester.
The present invention is directed to methods comprising adding ammonia, either as an ammonium salt or as a gas at, pressures below 0.01 MPa, to a sulfuryl fluoride solution to form the anion of bis(fluorosulfonyl)amine under conditions well suited for large-scale production. The bis(fluorosulfonyl)amine so produced can be isolated by methods described in the prior art, or isolated as an organic ion pair, such as an alkylammonium solid salt, or as an ionic liquid.
C07C 311/48 - Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
18.
IMPROVED SYNTHESIS OF TETRABUTYLAMMONIUM BIS(FLUOROSULFONYL)IMIDE AND RELATED SALTS
Methods of adding ammonia to a sulfuryl fluoride solution to form the anion of bis(fluorosulfonyl)amine under conditions well suited for large-scale production. The bis(fluorosulfonyl)amine so produced can be isolated by methods described in the prior art, or isolated as an organic ion pair, such as an alkylammonium solid salt, or as an ionic liquid. Using these conditions, purified product can be isolated in 95% yield as a tetrabutylammonium salt, [Bu4N]+[(FS02)2N]-. Gaseous NH3 is infused into the head space above a stirred solution ofS02F2, and/or slowly added as a solution of NH3 in a solvent. Alternatively, NH3 can be added as an ammonium salt, provided a base is present in the S02F2 solution or separately added to the solution. These liquid-addition embodiments offer some advantage, in that the accumulation of solid deposits on the walls of the reactor can be mitigated by subsurface introduction of the NH3.
The present invention is directed to methods comprising adding NH3 to a SO2F2 solution to directly form a FSO2NH2 and/or a salt of [FSO2NH]-, optionally quenching any unreacted NH3 present in the resulting mixture, and isolating the product from the resulting mixture.
