2,6-Difluorobenzoyl isocyanate → HCID 13578966, compound

HRID 1905451Notes

Reaction equation

HRID 1905451 reaction equation
[F:1][C:2]([F:16])([S:6]([C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12])(=[O:8])=[O:7])[CH:3]([F:5])[Cl:4].[F:17][C:18]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:19]=1[C:20]([N:22]=[C:23]=[O:24])=[O:21]>C1(C)C=CC=CC=1>[F:17][C:18]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:19]=1[C:20]([NH:22][C:23]([NH:12][C:11]1[CH:13]=[CH:14][CH:15]=[C:9]([S:6]([C:2]([F:1])([F:16])[CH:3]([F:5])[Cl:4])(=[O:7])=[O:8])[CH:10]=1)=[O:24])=[O:21]

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 13579036HCID 13579036, compound

Product 1

HCID 13578966HCID 13578966, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 20 ml of toluene was dissolved 20 g of 3-(1,1,2-trifluoro-2-chloroethylsulfonyl)aniline, amd 1.4 g of 2,6-difluorobenzoyl isocyanate was added to the solution, followed by stirring at room temperature (20° to 25° C.) for 2 hours. The reaction mixture was concentrated under reduced pressure, and the crystals which separated out were recovered by filtration, and washed with cyclohexane to give 3.3 g of N-(2,6-difluorobenzoyl)-N'-(3-(1,1,2-trifluoro-2-chloroethylsulfonyl)phenyl]urea (Compound No. 38), m.p. of 192°-194° C.

Workup

  1. additionwas added to the solution
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe crystals which separated out
  4. filtrationwere recovered by filtration
  5. washwashed with cyclohexane

Sources & evidence

ORD record
ord-fc07dab603354d9fa5355b19a98f0a88
Source dataset
uspto-grants-1989_06
Patent number
US04843100

Reaction notes

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