2,6-Difluorobenzoyl isocyanate → HCID 13578925, compound

HRID 1249539Notes

Reaction equation

HRID 1249539 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([S:9][CH:10]([F:12])[F:11])[CH:6]=[CH:5][C:3]=1[NH2:4].[F:13][C:14]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:15]=1[C:16]([N:18]=[C:19]=[O:20])=[O:17]>C1(C)C=CC=CC=1>[F:13][C:14]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:15]=1[C:16]([NH:18][C:19]([NH:4][C:3]1[CH:5]=[CH:6][C:7]([S:9][CH:10]([F:12])[F:11])=[CH:8][C:2]=1[F:1])=[O:20])=[O:17]

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 13579040HCID 13579040, compound

Product 1

HCID 13578925HCID 13578925, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 15 ml of toluene was dissolved 1.0 g of 2-fluoro-4-difluoromethylthioaniline, and 1.0 g of 2,6-difluorobenzoyl isocyanate was added dropwise to the solution at room temperature (20° to 25° C.). After the reaction was allowed to proceed at the same temperature for 30 minutes, the crystals, which separated out, were recovered by filtration and washed with toluene to give 1.5 g of N-(2,6-difluorobenzoyl)-N'-(2-fluoro-4-difluoromethylthiophenyl)urea (Compound No. 55). Recrystallization from acetone gave crystals having a melting point of 172°-173° C.

Workup

  1. additionwas added dropwise to the solution at room temperature (20° to 25° C.)
  2. customthe crystals, which separated out
  3. filtrationwere recovered by filtration
  4. washwashed with toluene

Sources & evidence

ORD record
ord-b63ecbf94e0941789b9f404910f993a5
Source dataset
uspto-grants-1986_12
Patent number
US04632938

Reaction notes

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