US4171302A
Expired / Lapsed
US
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Process for producing N-substituted amides
Assignee: Bayer CropScience SA
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Filing: 1977-11-21
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Granted: 1979-10-16
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Expires: 1997-11-21
Abstract
Abstract A process of preparing a N-substituted imide as disclosed, which is carried out in accordance with the equation: <IMAGE> wherein R is an alkyl radical containing 1 to 8 carbon atoms, or an aryl radical having 1 or 2 phenyl rings bearing up to 5 substituents selected from the group consisting of 1 to 3 atoms of halogen, 1 to 2 nitro, amino, or hydroxy groups, 1 to 4 alkyl radicals, and 1 to 2 alkoxy or alkylthiol radicals each containing 1 to 4 carbon atoms, or a hexyl radical, optionally substituted; R' is a single bond or a hydrocarbon chain containing from 1 to 4 carbon atoms, in which two contiguous carbons may belong to a phenyl ring, said hydrocarbon chain being saturated or unsaturated and optionally substituted and R'' is a hydrogen atom, an alkaline metal atom, an ammonium atom or a lower alkyl having 1 to 4 carbon atoms, wherein the cyclization of the amic acid, R-NH-CO-R'-COOR'' is carried out in the presence of a mixed catalyst which results from the association of the formula, A B, in which A is a strong inorganic or organic acid and B is a Lewis base.
Inventors
- 👤 Jean Abblard
- 👤 Michel Baudoin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 17:40
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/30; C07D207/34; C07D207/36; C07D207/40; C07D207/404; C07D207/44; C07D207/444; C07D207/448; C07D207/452
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
233 words
In a process of preparing an imide substituted on the nitrogen having the formula ##STR25## in which R is an alkyl radical containing 1 to 8 carbon atoms, or an aryl radical having 1 or 2 phenyl rings bearing up to 5 substituents selected from the group consisting of 1 to 3 atoms of halogen, 1 to 2 nitro, amino, or hydroxy groups, 1 to 4 alkyl radicals, and 1 to 2 alkoxy or alkylthiol radicals, each containing 1 to 4 carbon atoms, or a hexyl radical, R' is a single bond or a hydrocarbon chain containing from 1 to 4 carbon atoms, in which two contiguous carbons may belong to a phenyl ring, said hydrocarbon chain being saturated or unsaturated by cyclization of an amic acid of the formula: ##STR26## in which R and R' have the same meaning as above and R" is a hydrogen atom, an alkaline metal atom, an ammonium group, or a lower alkyl having 1 to 4 carbon atoms, in accordance with the equation: ##STR27## the improvement comprising carrying out the cyclization reaction in the presence of a mixed catalyst resulting from the association of the formula A B in which A is a strong inorganic or organic acid and B is a Lewis base selected from a member of the group consisting of monomethylformamide, dimethylformamide, monoethylformamide, dimethylacetamide, acetone, acetonitrile, N-methylpyrrolidone, dimethylsulfoxide, mesityl oxide, dioxane and tetrahydrofuran.
Claim 2
Dependent Claim
233 words
In a process of preparing an imide substituted on the nitrogen having the formula ##STR25## in which R is an alkyl radical containing 1 to 8 carbon atoms, or an aryl radical having 1 or 2 phenyl rings bearing up to 5 substituents selected from the group consisting of 1 to 3 atoms of halogen, 1 to 2 nitro, amino, or hydroxy groups, 1 to 4 alkyl radicals, and 1 to 2 alkoxy or alkylthiol radicals, each containing 1 to 4 carbon atoms, or a hexyl radical, R' is a single bond or a hydrocarbon chain containing from 1 to 4 carbon atoms, in which two contiguous carbons may belong to a phenyl ring, said hydrocarbon chain being saturated or unsaturated by cyclization of an amic acid of the formula: ##STR26## in which R and R' have the same meaning as above and R" is a hydrogen atom, an alkaline metal atom, an ammonium group, or a lower alkyl having 1 to 4 carbon atoms, in accordance with the equation: ##STR27## the improvement comprising carrying out the cyclization reaction in the presence of a mixed catalyst resulting from the association of the formula A B in which A is a strong inorganic or organic acid and B is a Lewis base selected from a member of the group consisting of monomethylformamide, dimethylformamide, monoethylformamide, dimethylacetamide, acetone, acetonitrile, N-methylpyrrolidone, dimethylsulfoxide, mesityl oxide, dioxane and tetrahydrofuran.
Claim 3
Dependent Claim
24 words
Process of preparation according to claim 1, in which A is a mono or poly-acid of a pK in water of at most 3.
Claim 4
Dependent Claim
51 words
Process for the preparation of an imide substituted on the nitrogen in accordance with claim 2, in which A is selected from the group which consists of sulfuric acid, an organosulfonic acid, phosphoric acid, an organophosphoric acid, and a mono- or dicarboxylic acid, optionally halogenated, containing 1 to 4 carbon atoms.
Claim 5
Dependent Claim
15 words
Process of preparation according to claim 3, in which A is sulfuric acid or paratoluene
Claim 6
Dependent Claim
11 words
Process according to claim 3, in which A is phosphoric acid.
Claim 7
Dependent Claim
11 words
Process according to claim 3, in which A is trifluoroacetic acid.
Claim 8
Dependent Claim
13 words
Process of preparation according to claim 3, in which A is maleic acid.
Claim 9
Dependent Claim
22 words
Process according to claim 1, in which the molar ratio of the acid to the amic acid is between 0.01 and 10.
Claim 10
Dependent Claim
22 words
Process according to claim 8, in which the molar ratio of the acid to the amic acid is between 0.1 and 1.
Claim 11
Dependent Claim
23 words
Process according to claim 1, in which the molar ratio of the Lewis base to the amic acid is between 0.01 and 1.
Claim 12
Dependent Claim
18 words
Process of preparation according to claim 1, in which the base/acid molar ratio is between 1 and 2.
Claim 13
Dependent Claim
15 words
Process according to claim 11 in which the base/acid molar ratio is equal to 1.
Claim 14
Dependent Claim
15 words
Process according to claim 11 in which the base/acid molar ratio is equal to 2.
Claim 15
Dependent Claim
25 words
Process according to claim 1, in which the catalyst is added in the amount of a catalyst/amic acid molar ratio of between 0.025 and 2.
Claim 16
Dependent Claim
25 words
Process according to claim 14, in which the catalyst is added in the amount of a catalyst/amic acid molar ratio of between 0.05 and 0.5.
Claim 17
Dependent Claim
17 words
Process according to claim 12 in which a 1:1 H 2 SO 4 /DMF complex is used.
Claim 18
Dependent Claim
17 words
Process according to claim 12, in which a 1:2 H 2 SO 4 /DMF complex is used.
Claim 19
Dependent Claim
16 words
Process according to claim 3, in which an H 2 SO 4 /N-methylpyrrolidone complex is used.
Claim 20
Dependent Claim
16 words
Process according to claim 4 in which an H 2 SO 4 /acetonitrile complex is used.
Claim 21
Dependent Claim
16 words
Process according to claim 4 in which an H 2 SO 4 /acetone complex is used.
Claim 22
Dependent Claim
15 words
Process according to claim 12 in which a 1:1 paratoluene sulfonic acid/DMF complex is used.
Claim 23
Dependent Claim
14 words
Process according to claim 1 in which the reaction is carried out without solvent.
Claim 24
Dependent Claim
27 words
Process according to claim 1 in which the reaction is carried out in an inert solvent medium of a boiling point of between 80° and 180° C.
Claim 25
Dependent Claim
13 words
Process according to claim 23, in which the solvent is an aromatic solvent.
Claim 26
Dependent Claim
11 words
Process according to claim 23, in which the solvent is toluene.
Claim 27
Dependent Claim
11 words
Process according to claim 23, in which the solvent is xylene.
Claim 28
Dependent Claim
19 words
Process according to claim 1 in which the reaction is carried out for half an hour to six hours.
Claim 29
Dependent Claim
21 words
Process according to claim 1 in which the reaction is carried out at a temperature of between 80° and 180° C.
Claim 30
Dependent Claim
23 words
Process of preparation according to claim 28, in which the reaction is carried out at a temperature of between 100° and 150° C.
References Cited (Backward Citations)
US3338919A
Cited
US3431276A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-10-15 | 1983-04-16 | 1983-10-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-10-15 | 1987-04-16 | 1987-10-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-10-15 | 1991-04-16 | 1991-10-16 | $7700.00 | Window Closed / Lapsed |