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

HRID 1701929Notes

Reaction equation

HRID 1701929 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 mole) of α,4-dichloro-2-(benzoyl)-benzenepropanenitrile, 17 g (0.14 mole) of potassium carbonate, 50.9 g (0.5 mole) of potassium bicarbonate and 510 ml of dimethyl sulfoxide was stirred at room temperature for 48 hr. The mixture was diluted with 1.5 l of water, and the resulting percipitate was collected by filtration. Recrystallization from a mixture of methylene chloride and ether gave off-white prisms, mp 89°-91°.

Workup

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

Sources & evidence

ORD record
ord-b7df8805869a45319537dcf3c861b1fe
Source dataset
uspto-grants-1983_04
Patent number
US04379765

Reaction notes

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