Benzenamine, 3,5-bis(trifluoromethyl)- → N-(3,5-bis-trifluoromethylphenyl)-N'-(chloroacetyl)-urea

HRID 28120

Reaction equation

[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[NH2:6].[Cl:16][CH2:17][C:18]([N:20]=[C:21]=[O:22])=[O:19]>C1(C)C=CC=CC=1>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:4]=[C:5]([NH:6][C:21]([NH:20][C:18](=[O:19])[CH2:17][Cl:16])=[O:22])[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Participants

Conditions

Temperature: 50 °C

Procedure

22.9 g (0.1 mol) of 3,5-bis-trifluoromethyl-aniline were dissolved in 150 ml of dry toluene. 11.9 g (0.1 mol) of chloroacetyl isocyanate in 50 ml of dry toluene were added. The mixture was stirred at 50° C. for 1 hour and then cooled to room temperature. The product which had precipitated was filtered off and rinsed with toluene/ligroin 1:2 and then dried. 26 g (74.5% of theory) of N-(3,5-bis-trifluoromethylphenyl)-N'-(chloroacetyl)-urea with a melting point of 170° C. were thus obtained.

Workup

temperaturecooled to room temperature
customThe product which had precipitated
filtrationwas filtered off
washrinsed with toluene/ligroin 1:2
customdried

Sources & evidence

ORD record: ord-4ee6114213f5458c87d8a1ed8c3494dc
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04225618

Linked notes

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