2-Fluoro-4-(1,1,2,2-tetrafluoroethylsulfanyl)aniline → HCID 20223572, compound

HRID 1249540Notes

Reaction equation

HRID 1249540 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].[C:16](Cl)(Cl)=[O:17].C1(C)C=CC=CC=1>>[F:1][C:2]1[CH:8]=[C:7]([S:9][C:10]([F:15])([F:14])[CH:11]([F:12])[F:13])[CH:6]=[CH:5][C:3]=1[N:4]=[C:16]=[O:17]

Participants

3

Reactant 2

HCID 1808102-Fluoro-4-(1,1,2,2-tetrafluoroethylsulfanyl)anilineHCID 19083224Phosgen toluene

Product 1

HCID 20223572HCID 20223572, compound

Procedure

To 140 ml of 4% phosgen-toluene solution was added 3.6 g of 2-fluoro-4-(1,1,2,2-tetrafluoroethylthio)aniline, and the mixture was heated under reflux for 3 hours. After the conclusion of the reaction, the reaction mixture was concentrated to dryness under reduced pressure to give 2-fluoro-4-(1,1,2,2-tetrafluoroethylthio)phenyl isocyanate as an oily material. The oily material was dissolved in 50 ml of xylene, and 1.5 g of 2,6-difluorobenzamide was added to the solution, followed by heating under reflux for 20 hours. After the conclusion of the reaction, the reaction mixture was cooled (0° C.), and the crystals which separated out were recovered by filtration, and further recrystallized from acetone to give N-(2,6-difluorobenzoyl)-N'-[2-fluoro-4-(1,1,2,2-tetrafluoroethylthio)phenyl]urea (Compound No. 1) as crystals having a m.p. of 177°-179° C. The resulting compound was found to show no decrease in melting point even when admixed with the authentic sample as obtained in Example 2.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customAfter the conclusion of the reaction
  4. concentrationthe reaction mixture was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-818e19aac8a14a6ba42d639c15e62c5f
Source dataset
uspto-grants-1986_12
Patent number
US04632938

Reaction notes

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