Toluene → HCID 15572312, compound

HRID 2286593Notes

Reaction equation

HRID 2286593 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([S:20][C:21]([F:24])([F:23])[F:22])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].C1(C)C=CC=CC=1.[C:38](Cl)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(Cl)Cl>[C:38]([N:11]1[C:12]([C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH:9]=[C:10]1[S:20][C:21]([F:23])([F:22])[F:24])(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 7412Benzoyl chlorideHCID 15572247HCID 15572247, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15572312HCID 15572312, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.1 g. (6 mmoles) of 4,5-bis-(4-fluorophenyl)-2-(trifluoromethylthio)pyrrole and 1.3 g. (12 mmoles) of potassium tert-butoxide in 60 ml. of toluene was heated to reflux with stirring and then cooled to room temperature under nitrogen. A solution of 1.7 g. of benzoyl chloride in 15 ml. of toluene was then added and the reaction mixture stirred overnight at room temperature. The mixture was diluted with methylene chloride, which was washed with 10% aqueous sodium bicarbonate solution, dried and evaporated. The residue was purified by chromatography on Fisher 100-200 mesh silica gel (eluted by hexane and then by mixtures of hexane/toluene), followed by recrystallization from ethanol/water to afford 1.8 g. of colorless crystals, m.p. 105.5°-106° C.

Workup

  1. additionA mixture of 2.1 g
  2. temperatureto reflux
  3. stirringthe reaction mixture stirred overnight at room temperature
  4. washwas washed with 10% aqueous sodium bicarbonate solution
  5. customdried
  6. customevaporated
  7. customThe residue was purified by chromatography on Fisher 100-200 mesh silica gel (
  8. washeluted by hexane
  9. customby mixtures of hexane/toluene), followed by recrystallization from ethanol/water
  10. customto afford 1.8 g

Sources & evidence

ORD record
ord-7002803bb6714e40943acd0a28e131ae
Source dataset
uspto-grants-1981_05
Patent number
US04267184

Reaction notes

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