Ammonia → Ethyl N-(2-carbamoyl-5-chlorophenyl)aminoacetate

HRID 569816Notes

Reaction equation

[Cl:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6](=[O:11])O[C:8](=O)[NH:9][C:4]=2[CH:3]=1.[H-].[Na+].BrC[C:18]([O:20][CH2:21][CH3:22])=[O:19].[NH3:23].Cl>CN(C)C=O>[C:6]([C:5]1[CH:12]=[CH:13][C:2]([Cl:1])=[CH:3][C:4]=1[NH:9][CH2:8][C:18]([O:20][CH2:21][CH3:22])=[O:19])(=[O:11])[NH2:23]

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of 7-chloro-2H-3,1-benzoxazine-2,4(1H)-dione (330 g) in N,N-dimethylformamide (3.3 l) was added sodium hydride (60% in mineral oil, 86.8 g) below 20° C. and the mixture was stirred at 5° C. for 30 minutes. To this solution was added ethyl bromoacetate (222 ml) at 10° C. over a 30-minute period and the resulting mixture was stirred at room temperature for 1.5 hours. To this reaction mixture was added 28% aqueous ammonia (696 ml) below 10° C. and the resulting mixture was stirred at 5° C. for 20 minutes. The mixture was poured into 1N hydrochloric acid (16.5 l). The precipitates were collected by filtration, and washed in turn with water (3 times) and diethyl ether to give ethyl N-(2-carbamoyl-5-chlorophenyl)aminoacetate (360 g).

Workup

stirringthe resulting mixture was stirred at room temperature for 1.5 hours
stirringthe resulting mixture was stirred at 5° C. for 20 minutes
filtrationThe precipitates were collected by filtration
washwashed in turn with water (3 times) and diethyl ether

Sources & evidence

ORD record: ord-9a66eb8ff95041c1ae746444b1df9af3
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04734419

Reaction notes

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