Water → HCID 14883681, compound

HRID 326818Notes

Reaction equation

HRID 326818 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)[C:11]([S:24][CH3:25])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.ClCCl.ClC1C=CC=C(C(OO)=[O:37])C=1.[OH2:40]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:22])([F:23])[F:21])[CH:15]=3)[C:11]([S:24]([CH3:25])(=[O:37])=[O:40])=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 15764727HCID 15764727, compound

Product 1

HCID 14883681HCID 14883681, compound

Procedure

1.5 g of 2-(4-chlorophenyl)-4-(3-trifluoromethylphenyl)-5-methylmercaptopyrimidine was added to 30 ml of dichloromethane. 2.0 g of m-chloroperbenzoic acid was added to the obtained reaction mixture under cooling in an ice-bath. Then, the resulting mixture was stirred at room temperature for 5 hours. After adding water, the mixture was extracted with dichloromethane. The organic phase was successively washed with a saturated aqueous solution of sodium sulfite and a saturated aqueous solution of sodium hydrogencarbonate. The solvent was distilled away under reduced pressure and the residue was subjected to column chromatography. Thus 1.5 g of 2-(4-chlorophenyl)-4-(3-trifluoromethylphenyl)-5-methanesulfonylpyrimidine was obtained (Compound 113).

Workup

  1. temperatureunder cooling in an ice-bath
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe organic phase was successively washed with a saturated aqueous solution of sodium sulfite
  4. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-cf274aecd34847cb83e361a25717dbeb
Source dataset
uspto-grants-1993_12
Patent number
US05270467

Reaction notes

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