Water → HCID 53995289, compound

HRID 1701997Notes

Reaction equation

HRID 1701997 reaction equation
Br[CH:2]([C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH:3]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])=[O:5].N1C=CN=N1.O>CN(C)C=O>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:3]([S:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)(=[O:5])=[O:6])=[CH:2][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 13048612HCID 13048612, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 53995289HCID 53995289, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-1-(4-chlorophenyl)-4,4-dimethyl-1-phenylsulfonylpentan-3-one (4.44 g) and triazole (2.76 g) were dissolved in dimethylformamide (30 ml), and the solution was refluxed for 2 hours. After cooling, it was poured into 100 ml of water and extracted with 100 ml of chloroform. The chloroform layer was washed for three times with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized in n-hexane, and the crystals were collected by filtration and dried to give 2.65 g of 1-(4-chlorophenyl)-4,4-dimethyl-1-phenylsulfonyl-1-penten-3-one. m.p. 135°-136° C.

Workup

  1. temperaturethe solution was refluxed for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with 100 ml of chloroform
  4. washThe chloroform layer was washed for three times with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized in n-hexane
  8. filtrationthe crystals were collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-c9b3495772fc4c1c91f8eeae1a3ad270
Source dataset
uspto-grants-1983_04
Patent number
US04379921

Reaction notes

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