2-Chloro-4-fluorobenzamide → HCID 20158493, compound

HRID 986265Notes

Reaction equation

HRID 986265 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Cl:12][C:13]1[CH:14]=[C:15]([N:26]=[C:27]=[O:28])[CH:16]=[CH:17][C:18]=1[O:19][C:20]([F:25])([F:24])[CH:21]([Cl:23])[F:22]>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.CO>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:6][C:27]([NH:26][C:15]1[CH:16]=[CH:17][C:18]([O:19][C:20]([F:24])([F:25])[CH:21]([Cl:23])[F:22])=[C:13]([Cl:12])[CH:14]=1)=[O:28])=[O:5]

Participants

5

Reactant 2

HCID 5228982-Chloro-4-fluorobenzamideHCID 201585052-Chloro-1-(2-chloro-1,1,2-trifluoroethoxy)-4-isocyanatobenzene

Product 1

HCID 20158493HCID 20158493, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 9809426Di-n-butyldilauryltinCatalystHCID 887MethanolSolvent

Procedure

3.47 g (0.02 mol) of 2-chloro-4-fluorobenzamide and 7.2 g (0.022 mol) of 3-chloro-4-(2-chloro-1,1,2-trifluoroethoxy)-phenyl isocyanate are melted for two hours at 180° C., in the presence of one drop of dibutyl-tin dilaurate. After the mixture has been cooled, the solid product is comminuted in hot methanol, and the product is filtered off under suction and dried. 7.2 g (76.5% of theory) of 1-(2-chloro-4-fluoro-benzoyl)-3-(3-chloro-4-(2-chloro-1,1,2-trifluoro-ethoxy)-phenyl)-urea of melting point 186° C. are obtained.

Workup

  1. temperatureAfter the mixture has been cooled
  2. filtrationthe product is filtered off under suction
  3. customdried

Sources & evidence

ORD record
ord-91a04bd4ad074531a1bd34723588db0c
Source dataset
uspto-grants-1987_12
Patent number
US04711905

Reaction notes

Loading…