2,6-Difluorobenzoyl isocyanate → N-(2,6-difluorobenzoyl)-N'-(2,4-difluoro-3-chloro-5-bromophenyl)-urea

HRID 1165410Notes

Reaction equation

HRID 1165410 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].[F:14][C:15]1[C:21]([Cl:22])=[C:20]([F:23])[C:19]([Br:24])=[CH:18][C:16]=1[NH2:17]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4]([NH:6][C:7]([NH:17][C:16]1[CH:18]=[C:19]([Br:24])[C:20]([F:23])=[C:21]([Cl:22])[C:15]=1[F:14])=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 198616345-Bromo-3-chloro-2,4-difluoroaniline

Product 1

HCID 19861636N-(2,6-difluorobenzoyl)-N'-(2,4-difluoro-3-chloro-5-bromophenyl)-urea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.75 g of 2,6-difluorobenzoyl isocyanate are added dropwise at room temperature, with stirring, to 5 g of 2,4-difluoro-3-chloro-5-bromoaniline dissolved in 50 ml of dry toluene, and the mixture is stirred for a further 5 hours. Approximately 75% of the solvent is then removed in a rotary evaporator. The residue is diluted with hexane and the resulting precipitate is filtered off with suction, washed with hexane and dried in vacuo. The title compound of formula ##STR14## is obtained in the form of colourless crystals; m.p. 225°-227° C.

Workup

  1. customApproximately 75% of the solvent is then removed in a rotary evaporator
  2. additionThe residue is diluted with hexane
  3. filtrationthe resulting precipitate is filtered off with suction
  4. washwashed with hexane
  5. customdried in vacuo

Sources & evidence

ORD record
ord-0f848796f2be48289d7bbe3350391ff7
Source dataset
uspto-grants-1990_03
Patent number
US04910018

Reaction notes

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