Phosgen toluene → HCID 20035715, compound

HRID 1905452Notes

Reaction equation

HRID 1905452 reaction equation
[C:1](Cl)(Cl)=[O:2].C1(C)C=CC=CC=1.[F:12][C:13]1[CH:19]=[C:18]([S:20]([C:23]([F:28])([F:27])[CH:24]([F:26])[F:25])(=[O:22])=[O:21])[CH:17]=[CH:16][C:14]=1[NH2:15]>>[F:12][C:13]1[CH:19]=[C:18]([S:20]([C:23]([F:27])([F:28])[CH:24]([F:25])[F:26])(=[O:22])=[O:21])[CH:17]=[CH:16][C:14]=1[N:15]=[C:1]=[O:2]

Participants

3

Reactant 2

HCID 19083224Phosgen tolueneHCID 20035714HCID 20035714, compound

Product 1

HCID 20035715HCID 20035715, compound

Procedure

To 4% phosgen-toluene solution was added 4.0 g of 2-fluoro-4-(1,1,2,2-tetrafluoroethylsulfonyl)aniline, followed by heating under reflux for 3 hours. After the completion of the reaction, the reaction mixture was concentrated to dryness under reduced pressure to give 2-fluoro-4-(1,1,2,2-tetrafluoroethylsulfonyl)phenyl isocyanate as an oily material. In 50 ml of xylene was dissolved the oily material, and 1.5 of 2.6-difluorobenzamide was added to the solution, followed by heating under reflux for 20 hours. After the completion of the reaction, the reaction mixture was cooled to 0° C., and the crystals which separated out was recovered by filtration and recrystallized from acetone to give N-(2,6-difluorobenzoyl)-N'-[2-fluoro-4-(1,1,2,2-tetrafluoroethylsulfonyl)phenyl]urea (Compound No. 5) as crystals having a melting point of 186°-187° C. The melting point of the crystals did not descend in a mixed examination with the product of Example 4.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. customAfter the completion of the reaction
  4. concentrationthe reaction mixture was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-81aab2760e1a49359410599dc7215575
Source dataset
uspto-grants-1989_06
Patent number
US04843100

Reaction notes

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