3,4-Dichloroaniline → 2-Chloro-N-[(3,4-dichlorophenyl)carbamoyl]-4-fluorobenzamide

HRID 986264Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

3.24 g (0.02 mol) of 3,4-dichloroaniline are dissolved in 60 ml of dry toluene, and 3.99 g (0.02 mol) of 2-chloro-4-fluoro-benzoyl isocyanate are added in the absence of moisture. The mixture is stirred for one hour at 80° C. and then cooled to 20°-25° C. The precipitate which separates out is filtered off under suction and dried in vacuo at 100° C. 6.8 g (94% of theory) of 1-(2-chloro-4-fluoro-benzoyl)-3-(3,4-dichlorophenyl)-urea of melting point 208° C. are obtained.

Workup

temperaturecooled to 20°-25° C
filtrationThe precipitate which separates out is filtered off under suction
customdried in vacuo at 100° C

Sources & evidence

ORD record: ord-38549dc34926424faeddb41ba732d3f2
Source dataset: uspto-grants-1987_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04711905

Reaction notes

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