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US4479901A
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Fluorination of carbanions with N-fluoro-N-alkylsulfonamides
Assignee: EIDP Inc
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Filing: 1983-08-15
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Granted: 1984-10-30
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Expires: 2003-08-15
Abstract
Abstract Process for fluorinating an organic carbanion, which process comprises contacting and reacting, in a dry inert atmosphere, the compound of the formula selected from ##STR1## wherein ##STR2## is the carbanion, M is a counter ion, and X is a halide and a selected N-flouro-N-alkylsulfonamide.
Inventors
- 👤 William E. Barnette
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 20:37
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/62; C07B; C07B39/00; C07C17/00; C07C17/093; C07C201/00; C07C201/06; C07C201/12; C07C41/00; C07C41/01; C07C41/18; C07C41/22; C07C45/00; C07C45/51; C07C45/54; C07C45/61; C07C45/63; C07C49/00; C07C49/385; C07C49/457; C07C49/463
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
122 words
Process for fluorinating an organic carbanion, which process comprises contacting and reacting, in a dry inert atmosphere, the compound of the formula selected from ##STR13## and the N-fluoro-N-alkylsulfonamide of the formula ##STR14## wherein R is C 1-30 branched or straight chain alkyl, C 3-30 cycloalkyl, ar(C 1-10 alkyl) or aryl wherein ar and aryl are C 6-14 ; R 1 is C 1-30 branched or straight chain alkyl, C 3-30 cycloalkyl or ar(C 1-10 alkyl) wherein ar is C 6-14 ; ##STR15## is an organic carbanion other than a β-diketo enolate; M.sup.⊕ is an alkali metal or tetraalkylammonium cation; M.sup. +2 is an alkaline earth metal cation; X.sup.⊖ is fluoride, chloride, bromide or iodide; and F is 19 F or 18 F.
Claim 2
Dependent Claim
122 words
Process for fluorinating an organic carbanion, which process comprises contacting and reacting, in a dry inert atmosphere, the compound of the formula selected from ##STR13## and the N-fluoro-N-alkylsulfonamide of the formula ##STR14## wherein R is C 1-30 branched or straight chain alkyl, C 3-30 cycloalkyl, ar(C 1-10 alkyl) or aryl wherein ar and aryl are C 6-14 ; R 1 is C 1-30 branched or straight chain alkyl, C 3-30 cycloalkyl or ar(C 1-10 alkyl) wherein ar is C 6-14 ; ##STR15## is an organic carbanion other than a β-diketo enolate; M.sup.⊕ is an alkali metal or tetraalkylammonium cation; M.sup. +2 is an alkaline earth metal cation; X.sup.⊖ is fluoride, chloride, bromide or iodide; and F is 19 F or 18 F.
Claim 3
Dependent Claim
17 words
Process of claim 1 wherein the contacting and reacting are carried out at -78° to 0° C.
Claim 4
Dependent Claim
18 words
Process of claim 1 wherein the contacting and reacting are carried out at about 0° to 40° C.
Claim 5
Dependent Claim
14 words
Process of claim 1 wherein the compound is ##STR16## wherein M.sup.⊕ is alkali metal.
Claim 6
Dependent Claim
9 words
Process of claim 1 wherein the compound is ##STR17##
Claim 7
Dependent Claim
16 words
Process of claim 1 wherein the mole ratio of alkylsulfonamide to carbanion ##STR18## is about 1:1.
Claim 8
Dependent Claim
11 words
Process of claim 1 wherein there is present an inert solvent.
Claim 9
Dependent Claim
12 words
Process of claim 7 wherein the inert solvent is a nonpolar solvent.
Claim 10
Dependent Claim
12 words
Process of claim 7 wherein the inert solvent is a polar solvent.
Claim 11
Dependent Claim
14 words
Process of claim 8 wherein the solvent is selected from toluene, benzene and hexane.
Claim 12
Dependent Claim
15 words
Process of claim 9 wherein the solvent is selected from diethyl ether, tetrahydrofuran and dimethoxyethane.
Claim 13
Dependent Claim
9 words
Process of claim 1 wherein F is 18 F.
Claim 14
Dependent Claim
1 words
N-Fluoro-N-neopentyl-p-toluenesulfonamide.
Claim 15
Dependent Claim
1 words
N-Fluoro-N-neopentyl-p-toluenesulfonamide.
Claim 16
Dependent Claim
1 words
N-Fluoro-N-(exo-2-norbornyl)-p-toluenesulfonamide.
Claim 17
Dependent Claim
1 words
N-Fluoro-N-(exo-2-norbornyl)-p-toluenesulfonamide.
Claim 18
Dependent Claim
1 words
N-Fluoro-N-(endo-2-norbornyl)-p-toluenesulfonamide.
Claim 19
Dependent Claim
1 words
N-Fluoro-N-(endo-2-norbornyl)-p-toluenesulfonamide.
Claim 20
Dependent Claim
1 words
N-Fluoro-N-neopentyl-n-butylsulfonamide.
Claim 21
Dependent Claim
1 words
N-Fluoro-N-neopentyl-n-butylsulfonamide.
References Cited (Backward Citations)
US4232016A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-10-30 | 1988-04-30 | 1988-10-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-10-30 | 1992-04-30 | 1992-10-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-10-30 | 1996-04-30 | 1996-10-30 | $7700.00 | Window Closed / Lapsed |