US3971821A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Production of aminobenzaldehydes
Assignee: BASF SE
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Filing: 1974-12-09
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Granted: 1976-07-27
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Expires: 1994-12-09
Abstract
Abstract Aminobenzaldehyde compounds and a process for their production by the reaction of an aniline with a formamide in the presence of an acid halide with or without a following reaction with a nitrogen compound. The products are starting materials for the production of optical brighteners, dyes, plant protection agents and medicaments.
Inventors
- 👤 Hans Baumann
- 👤 Klaus Grychtol
- 👤 Andreas Oberlinner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 08:58
CPC Classifications
C; C07; C07C; C07C251/00; C07C251/72
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
197 words
A process for the production of an aminobenzaldehyde compound of the formula ##SPC27## wherein R 1 and R 2 may be identical or different and each is alkyl of 1 to 8 carbon atoms or aralkyl of 7 to 12 carbon atoms; and R 3 is nitro, cyano or ##EQU11## in which R 4 is alkyl of 1 to 8 carbon atoms, cyclopentyl, aralkyl of 7 to 12 carbon atoms or phenyl; which process comprises reacting an aniline of the formula ##SPC28## wherein R 1 , R 2 and R 3 have the above-noted meanings, in the presence of an acid halide of phosphorous acid, phosphoric acid, carbonic acid, oxalic acid, sulfurous acid or sulfuric acid with a formamide of the formula ##EQU12## wherein R 5 and R 6 may be identical or different and each is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl, or R 5 and R 6 together with the adjacent nitrogen atom may further form a heterocyclic ring member selected from the group consisting of piperidine, pyrrolidine and morpholine, with the proviso that said R 1 to R 6 may further contain substituents which are inert under the reaction conditions.
Claim 2
Dependent Claim
197 words
A process for the production of an aminobenzaldehyde compound of the formula ##SPC27## wherein R 1 and R 2 may be identical or different and each is alkyl of 1 to 8 carbon atoms or aralkyl of 7 to 12 carbon atoms; and R 3 is nitro, cyano or ##EQU11## in which R 4 is alkyl of 1 to 8 carbon atoms, cyclopentyl, aralkyl of 7 to 12 carbon atoms or phenyl; which process comprises reacting an aniline of the formula ##SPC28## wherein R 1 , R 2 and R 3 have the above-noted meanings, in the presence of an acid halide of phosphorous acid, phosphoric acid, carbonic acid, oxalic acid, sulfurous acid or sulfuric acid with a formamide of the formula ##EQU12## wherein R 5 and R 6 may be identical or different and each is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl, or R 5 and R 6 together with the adjacent nitrogen atom may further form a heterocyclic ring member selected from the group consisting of piperidine, pyrrolidine and morpholine, with the proviso that said R 1 to R 6 may further contain substituents which are inert under the reaction conditions.
Claim 3
Dependent Claim
30 words
A process as claimed in claim 1 wherein the reaction is carried out with from 1 mole to 4 moles of starting material (III) per mole of starting material (II).
Claim 4
Dependent Claim
29 words
A process as claimed in claim 1 wherein the reaction is carried out with from 1 mole to 8 moles of acid halide per mole of starting material (II).
Claim 5
Dependent Claim
30 words
A process as claimed in claim 1 wherein the reaction is carried out with oxalyl chloride, oxalyl bromide, thionyl chloride, phosphorus trichloride, phosphorus tribromide, sulfuryl chloride, phosphorus oxychloride or phosgene.
Claim 6
Dependent Claim
21 words
A process as claimed in claim 1 wherein the reaction is carried out at a temperature of from -10° to +120°C.
Claim 7
Dependent Claim
21 words
A process as claimed in claim 1 wherein the reaction is carried out at a temperature of from +20° to +80°C.
Claim 8
Dependent Claim
42 words
A process as claimed in claim 1 wherein the reaction is carried out in the presence of an organic solvent which is inert under the reaction conditions in an amount of from 10 to 1000% by weight based on starting material (II).
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) | 1979-07-27 | 1980-01-26 | 1980-07-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-07-27 | 1984-01-26 | 1984-07-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-07-27 | 1988-01-26 | 1988-07-27 | $7700.00 | Window Closed / Lapsed |