2-Fluoro-4-(1,1,2,2-tetrafluoroethylsulfanyl)aniline → 2,6-Difluoro-N-(((2-fluoro-4-((1,1,2,2-tetrafluoroethyl)thio)phenyl)amino)carbonyl)benzamide

HRID 1249538Notes

Reaction equation

HRID 1249538 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([S:9][C:10]([F:15])([F:14])[CH:11]([F:13])[F:12])[CH:6]=[CH:5][C:3]=1[NH2:4].[F:16][C:17]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:18]=1[C:19]([N:21]=[C:22]=[O:23])=[O:20]>C1(C)C=CC=CC=1>[F:16][C:17]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:18]=1[C:19]([NH:21][C:22]([NH:4][C:3]1[CH:5]=[CH:6][C:7]([S:9][C:10]([F:15])([F:14])[CH:11]([F:12])[F:13])=[CH:8][C:2]=1[F:1])=[O:23])=[O:20]

Participants

4

Reactant 2

HCID 1808102-Fluoro-4-(1,1,2,2-tetrafluoroethylsulfanyl)anilineHCID 27333692,6-Difluorobenzoyl isocyanate

Product 1

HCID 1807932,6-Difluoro-N-(((2-fluoro-4-((1,1,2,2-tetrafluoroethyl)thio)phenyl)amino)carbonyl)benzamideYield 85.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 20 ml of toluene was dissolved 1.0 g of 2-fluoro-4-(1,1,2,2-tetrafluoroethylthio)aniline, and 0.8 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-(1,1,2,2-tetrafluoro-ethylthio)phenyl]urea (Compound No. 1), m.p. of 177°-179° 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-71860a894642499e89cea70e22ac225d
Source dataset
uspto-grants-1986_12
Patent number
US04632938

Reaction notes

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