US3917688A
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Process for the preparation of N-monofluoro-acid amides, N-monofluoro and N,N-difluoro-tertiary amines
Assignee: Research Institute for Medicine and Chemistry Inc
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Filing: 1973-06-26
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Granted: 1975-11-04
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Expires: 1993-06-26
Abstract
Abstract The preparation of a range of N-fluorinated amides and amines by treatment of an acid amide with a hypofluorite in which the fluoroxy group is bonded to an inert electron attracting group is described, suitable fluorinating agents including fluoroalkyl hypofluorites such as trifluoromethyl hypofluorite. Primary and secondary amides are converted into N-monofluoro amides, which may be cleaved hydrolytically to yield N-monofluoroamines; Nmonofluoro carboxamide products may also be cleaved fluorolytically, e.g. by treatment with excess hypofluorite, to yield N,N-difluoroamines. Tertiary amides may be converted directly into N-fluorinated amines, this last conversion preferably being effected under acid conditions.
Inventors
- 👤 Derek Harold Richard Barton
- 👤 Robert Henry Hesse
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 04:35
CPC Classifications
C; C07; C07B; C07B39/00
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
41 words
A PROCESS FOR THE PREPARATION OF A COMPOUND SELECTED FROM THE GROUP CONSISTING OF N - MONOFLUORO-ACID AMIDES, N - MONOFLUORO - AND N, N-DIFLUORO - TERTIARY AMINES WHICH COMPRISES REACTING IN POLAR ORGANIC SOLVENT AN ACID AMIDE OF THE FORMULA
Claim 2
Dependent Claim
41 words
A PROCESS FOR THE PREPARATION OF A COMPOUND SELECTED FROM THE GROUP CONSISTING OF N - MONOFLUORO-ACID AMIDES, N - MONOFLUORO - AND N, N-DIFLUORO - TERTIARY AMINES WHICH COMPRISES REACTING IN POLAR ORGANIC SOLVENT AN ACID AMIDE OF THE FORMULA
Claim 3
Dependent Claim
24 words
The process of claim 1 where R3 is hydrogen and R2 is other than hydrogen, to yield an n- monofluoro-acid amide of the formula
Claim 4
Dependent Claim
24 words
A process as claimed in claim 2 wherein the N-monofluoro acid amide product is fluorinated further to yield an N,N-difluoroamine of formula R2NF2 (III)
Claim 5
Dependent Claim
25 words
A process as claimed in claim 2 wherein the N-monofluoro acid amide is subjected to hydrolytic cleavage to yield an N-monofluoroamine of formula R2NHF (IV)
Claim 6
Dependent Claim
28 words
The process of claim 2 wherein the acid amide material is N -adamant -1 - ylacetamide to yield N - adamant - 1 - yl - N -fluoroacetamide.
Claim 7
Dependent Claim
37 words
The process of claim 1, wherein the starting acid amide is a tertiary amide and a N - monofluoroamine of the formula R2R3NF, wherein R2 and R3 are other than hydrogen, or a salt thereof is formed.
Claim 8
Dependent Claim
30 words
A process as claimed in claim 6 wherein the reaction is effected in the presence of an acid selected from the group consisting of mineral acids and strong organic acids.
Claim 9
Dependent Claim
37 words
A process as claimed in claim 1 wherein the acid amide is reacted with at least two equivalents of the hypofluorite to yield directly an N,N - difluoroamine without separation of the intermediate N - monofluoro carboxamide.
Claim 10
Dependent Claim
13 words
A process as claimed in claim 1 wherein the hypofluorite is trifluoromethyl hypofluorite.
Claim 11
Dependent Claim
52 words
A process as claimed in claim 1 wherein R1, R2 and R3 are each methyl, ethyl, propyl, butyl, hexyl, decyl, pentadecyl, heptadecyl, eicosyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, benzyl, phenethyl, phenyl, naphthyl, or any of the above groups substituted by oxo, nitro, cyano, halo, hydroxy, esterified hydroxy, sulphonyl, lower alkoxy, aralkoxy or aryloxy.
Claim 12
Dependent Claim
19 words
The process of claim 1, wherein the reaction temperature for the fluorination is from -78* to + 40*C ;
Claim 13
Dependent Claim
35 words
The process of claim 1, wherein the hypofluorite is selected from the group consisting trifluoromethyl, perfluoropropyl, perfluoroisopropyl, perfluoro - t - butyl, monochlorohexafluoropropyl and perfluorot -pentyl hypofluorites, 1, 2 - difluoroxytetrafluoroethane, difluoroxydifluoromethane, and fluoroxysulphur pentafluoride.
Claim 14
Dependent Claim
50 words
A process for the preparation of an N - monofluoro-carboxylic acid amide, comprising monofluorinating a secondary carboxylic acid amide by reaction with a hypoflurite having the formula ROF where R represents a lower fluoralky group containing at least two fluorine atoms per carbon atom or a fluorinated covalent inorganic group.
Claim 15
Dependent Claim
50 words
A process for the preparation of an N - monofluoro-carboxylic acid amide, comprising monofluorinating a secondary carboxylic acid amide by reaction with a hypoflurite having the formula ROF where R represents a lower fluoralky group containing at least two fluorine atoms per carbon atom or a fluorinated covalent inorganic group.
Claim 16
Dependent Claim
49 words
A process for the preparation of an N - monofluoro -tertiary amine, comprising monofluorinating an acid tertiary carboxamide by reaction with a hypofluorite having the formula ROF where R represents a lower fluoroalkyl group containing at least two fluorine atoms per carbon atom or a fluorinated covalent inorganic group.
Claim 17
Dependent Claim
49 words
A process for the preparation of an N - monofluoro -tertiary amine, comprising monofluorinating an acid tertiary carboxamide by reaction with a hypofluorite having the formula ROF where R represents a lower fluoroalkyl group containing at least two fluorine atoms per carbon atom or a fluorinated covalent inorganic group.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-11-03 | 1979-05-05 | 1979-11-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-11-03 | 1983-05-05 | 1983-11-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-11-03 | 1987-05-05 | 1987-11-04 | $7700.00 | Window Closed / Lapsed |