Dimethyl Sulfoxide → 3-(2-Benzoyl-4-chlorophenyl)prop-2-enenitrile

HRID 1903621Notes

Reaction equation

HRID 1903621 reaction equation
Cl[CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]#[N:4].C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[K+].CS(C)=O>O>[C:13]([C:7]1[CH:8]=[C:9]([Cl:12])[CH:10]=[CH:11][C:6]=1[CH:5]=[CH:2][C:3]#[N:4])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 516893Potassium BicarbonateHCID 13067144alpha,4-Dichloro-2-(benzoyl)benzenepropanenitrile

Product 1

HCID 543140203-(2-Benzoyl-4-chlorophenyl)prop-2-enenitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 50.9 g (0.168 mol) of α,4-dichloro-2-(benzoyl)benzenepropanenitrile, 17 g (0.14 mol) of potassium carbonate, 50.9 g (0.5 mol) of potassium bicarbonate and 510 ml of dimethyl sulfoxide was stirred at room temperature for 48 hours. The mixture was diluted with 1.5 liters of water, and the resulting precipitate was collected by filtration. Recrystallization from a mixture of methylene chloride and ether gave off-white prisms, mp 89°-91° C.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customRecrystallization
  3. additionfrom a mixture of methylene chloride and ether
  4. customgave off-white prisms, mp 89°-91° C.

Sources & evidence

ORD record
ord-a32baa2c8f574c999ab23e8778d6bde2
Source dataset
uspto-grants-1984_03
Patent number
US04436662

Reaction notes

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