US4101576A
Expired / Lapsed
US
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2-Carbamylmethyl-or (diethylcarbamyl)methyl-amino-4-hydroxy toluene and process for preparing the same
Assignee: L'Oréal SA
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Filing: 1977-01-25
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Granted: 1978-07-18
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Expires: 1997-01-25
Abstract
Abstract The dye coupling compounds 2-carbamylmethylamino-4-hydroxy toluene and 2-diethylcarbamylmethylamino-4-hydroxy toluene.
Inventors
- 👤 Gregoire Kalopissis
- 👤 Andree Bugaut
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 23:00
CPC Classifications
A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/40; A61K8/42; A61Q; A61Q5/00; A61Q5/10
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
332 words
A process for preparing 2-amino-4-hydroxy toluene comprising: (1) reacting paracresol in the presence of pyridine with methane sulfochloride at a temperature of about -2° to 5° C to produce a compound having the formula ##STR6## the molar ratio of said cresol to said sulfochloride being 2.0:2.4; (2) cooling the compound from step (1) in the presence of a mixture of sufficient ice and chlorohydric acid present in a molar ratio of 14.2 moles per 2 moles of cresol; (3) recovering the product of step (2) from the reaction mass and dissolving said separated product at a temperature of 0° - 5° C in concentrated sulfuric acid; (4) nitrating the dissolved product of step (3) with a nitrating agent comprising a mixture of nitric acid and sulfuric acid in a ratio of 4.7 cm 3 :3.8 cm 3 , respectively, at a temperature of 0° - 5° C to produce a product having the formula ##STR7## (5) pouring the reaction mixture from step (4) over ice to recover the nitrated product of step (4); (6) reducing the --NO 2 substituent on the nitrated product recovered from step (5) to --NH 2 with a reducing agent comprising a mixture of tin and hydrochloric acid; (7) cooling the reaction mixture from step (6) thereby precipitating 2-amino-4-mesyloxy toluene as the chlorostannate thereof; (8) drying the precipitate from step (7) and dissolving said dried precipitate in water; (9) subjecting the dissolved precipitate from step (8) to a current of hydrogen sulfide whereby tin sulfide is formed and thereafter removed by filtration; (10) vacuum concentrating the filtrate from step (9) and cooling said concentrated filtrate thereby precipitating the hydrochloride of 2-amino-4-mesyloxy toluene; (11) reacting the hydrochloride of 2-amino-4-mesyloxy toluene from step (10) in an inert nitrogen atmosphere with NaOH in amounts of 125 cc per 0.5 mole of said hydrochloride of 2-amino-4-mesyloxy toluene under reflux for about 2 hours; and (12) cooling the reaction mixture from step (11) and neutralizing the same with HCl thereby producing 2-amino-4-hydroxy toluene.
Claim 2
Dependent Claim
332 words
A process for preparing 2-amino-4-hydroxy toluene comprising: (1) reacting paracresol in the presence of pyridine with methane sulfochloride at a temperature of about -2° to 5° C to produce a compound having the formula ##STR6## the molar ratio of said cresol to said sulfochloride being 2.0:2.4; (2) cooling the compound from step (1) in the presence of a mixture of sufficient ice and chlorohydric acid present in a molar ratio of 14.2 moles per 2 moles of cresol; (3) recovering the product of step (2) from the reaction mass and dissolving said separated product at a temperature of 0° - 5° C in concentrated sulfuric acid; (4) nitrating the dissolved product of step (3) with a nitrating agent comprising a mixture of nitric acid and sulfuric acid in a ratio of 4.7 cm 3 :3.8 cm 3 , respectively, at a temperature of 0° - 5° C to produce a product having the formula ##STR7## (5) pouring the reaction mixture from step (4) over ice to recover the nitrated product of step (4); (6) reducing the --NO 2 substituent on the nitrated product recovered from step (5) to --NH 2 with a reducing agent comprising a mixture of tin and hydrochloric acid; (7) cooling the reaction mixture from step (6) thereby precipitating 2-amino-4-mesyloxy toluene as the chlorostannate thereof; (8) drying the precipitate from step (7) and dissolving said dried precipitate in water; (9) subjecting the dissolved precipitate from step (8) to a current of hydrogen sulfide whereby tin sulfide is formed and thereafter removed by filtration; (10) vacuum concentrating the filtrate from step (9) and cooling said concentrated filtrate thereby precipitating the hydrochloride of 2-amino-4-mesyloxy toluene; (11) reacting the hydrochloride of 2-amino-4-mesyloxy toluene from step (10) in an inert nitrogen atmosphere with NaOH in amounts of 125 cc per 0.5 mole of said hydrochloride of 2-amino-4-mesyloxy toluene under reflux for about 2 hours; and (12) cooling the reaction mixture from step (11) and neutralizing the same with HCl thereby producing 2-amino-4-hydroxy toluene.
Claim 3
Dependent Claim
129 words
The process of claim 1 which also includes dissolving the 2-amino-4-hydroxy toluene resulting from step (12) under reflux in a 50% aqueous alcoholic solution in amounts of 0.405 mole of said 2-amino-4-hydroxy toluene per 330 cm 3 of said aqueous alcoholic solution, adding calcium carbonate to the resulting solution in amounts of 21 g of said calcium carbonate per 0.405 mole of said 2-amino 4-hydroxy toluene, and while agitating the resulting mixture adding thereto an aqueous solution of chloroacetamide in amounts of 0.42 mole of chloroacetamide in 345 cm 3 of water per 0.405 mole of said 2-amino-4-hydroxy toluene, continuing, reflux of the resulting reaction mixture for an hour, filtering said reaction mixture while boiling, cooling and drying the resulting filtrate thereby yielding 2-carbamylmethylamino-4-hydroxy toluene having the formula ##STR8##
Claim 4
Dependent Claim
129 words
The process of claim 1 which also includes dissolving the 2-amino-4-hydroxy toluene resulting from step (12) under reflux in a 50% aqueous alcoholic solution in amounts of 0.05 mole of said 2-amino-4-hydroxy toluene per 40 cm 3 of said aqueous alcoholic solution, adding calcium carbonate to the resulting solution in amounts of 2.6 g of said calcium carbonate per 0.05 mole of said 2-amino-4-hydroxy toluene, and while agitating the resulting mixture adding thereto an aqueous solution of N,N-diethylchloracetamide in amounts of 0.051 mole of N,N-diethylchloracetamide in 50 cm 3 of water per 0.05 mole of said 2-amino-4-hydroxy toluene, continuing reflux of the resulting reaction mixture for an hour, filtering said reaction mixture while boiling, cooling and drying the resulting filtrate thereby yielding 2-(diethylcarbamyl) methylamino-4-hydroxy toluene having the formula ##STR9##
Claim 5
Dependent Claim
2 words
2-carbamylmethylamino-4-hydroxy toluene.
Claim 6
Dependent Claim
2 words
2-carbamylmethylamino-4-hydroxy toluene.
Claim 7
Dependent Claim
3 words
2-(diethylcarbamyl) methylamino-4-hydroxy toluene.
Claim 8
Dependent Claim
3 words
2-(diethylcarbamyl) methylamino-4-hydroxy toluene.
References Cited (Backward Citations)
US3563684A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-07-17 | 1982-01-16 | 1982-07-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-07-17 | 1986-01-16 | 1986-07-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-07-17 | 1990-01-16 | 1990-07-18 | $7700.00 | Window Closed / Lapsed |