4-Chloro-3-(trifluoromethyl)aniline → Propanoic acid, 2-((((4-chloro-3-(trifluoromethyl)phenyl)amino)carbonyl)amino)-2-methyl-, methyl ester

HRID 224944

Reaction equation

HRID 224944 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:12])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH3:13][O:14][C:15](=[O:22])[C:16]([N:19]=[C:20]=[O:21])([CH3:18])[CH3:17]>>[CH3:13][O:14][C:15](=[O:22])[C:16]([CH3:18])([CH3:17])[NH:19][C:20](=[O:21])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:12])=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1

Participants

3

Reactant 2

HCID 675744-Chloro-3-(trifluoromethyl)anilineHCID 2769374Methyl 2-isocyanato-2-methylpropanoate

Product 1

HCID 3054076Propanoic acid, 2-((((4-chloro-3-(trifluoromethyl)phenyl)amino)carbonyl)amino)-2-methyl-, methyl ester

Conditions

Temperature
80 °C

Procedure

9.75 g (50 mmol) of 5-amino-2-chlorobenzotrifluoride and 7.15 g (50 mmol) of 2-isocyanato-2-methylpropionic acid methyl ester were admixed and melted at 80° C. The melt was maintained at 80° C. for 30 minutes. The resulting product which was crystallized during the process, was recrystallized from isopropanol/methylene chloride and dried at 50° C. for 20 hours, under greatly reduced pressure, to yield N-[(3-Trifluoromethyl-4-chloro-phenyl)-carbamoyl]-2-methylalanine methyl ester, m.p. 141°-142° C.

Workup

  1. customThe resulting product which was crystallized during the process
  2. customwas recrystallized from isopropanol/methylene chloride
  3. customdried at 50° C. for 20 hours, under greatly reduced pressure

Sources & evidence

ORD record
ord-09d5c0bada2a410b9133642cd0849512
Source dataset
uspto-grants-1980_11
Patent number
US04234736

Linked notes

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