3,5-Dichloro-4-fluoroaniline → N-[(3,5-dichloro-4-fluorophenyl)-carbamoyl]-2-methylalanine methyl ester

HRID 647125

Reaction equation

HRID 647125 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:10])[C:8]=1[F:9])[NH2:5].[CH3:11][O:12][C:13](=[O:20])[C:14]([N:17]=[C:18]=[O:19])([CH3:16])[CH3:15]>>[CH3:11][O:12][C:13](=[O:20])[C:14]([CH3:16])([CH3:15])[NH:17][C:18](=[O:19])[NH:5][C:4]1[CH:3]=[C:2]([Cl:1])[C:8]([F:9])=[C:7]([Cl:10])[CH:6]=1

Participants

3

Reactant 2

HCID 759483,5-Dichloro-4-fluoroanilineHCID 2769374Methyl 2-isocyanato-2-methylpropanoate

Product 1

HCID 20439133N-[(3,5-dichloro-4-fluorophenyl)-carbamoyl]-2-methylalanine methyl ester

Procedure

3-(3,5-dichloro-4-phenyl)-5,5-dimethylhydantoin, which melts at 175°-176°, is obtained in the manner indicated in Example 1 from 3,5-dichloro-4-fluoro-aniline and 2-isocyanato-2-methylpropionic acid methyl ester and after crystallizing from ether/petroleum ether. The N-[(3,5-dichloro-4-fluorophenyl)-carbamoyl]-2-methylalanine methyl ester intermediately formed is not isolated.

Workup

  1. customafter crystallizing from ether/petroleum ether

Sources & evidence

ORD record
ord-58628825cad64a3ea3319cdf6ad7b0cf
Source dataset
uspto-grants-1983_10
Patent number
US04407814

Linked notes

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