Thionyl Chloride → 2-Propenoyl chloride, 2-cyano-3,3-diphenyl-

HRID 1758358Notes

Reaction equation

HRID 1758358 reaction equation
[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]([C:12]#[N:13])[C:9](O)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:22])=O>C1(C)C=CC=CC=1>[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]([C:12]#[N:13])[C:9]([Cl:22])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 98378162-Cyano-3,3-diphenyl-2-propenoic acid

Product 1

HCID 122409102-Propenoyl chloride, 2-cyano-3,3-diphenyl-Yield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 100 ml. of toluene solution containing 50 g. (0.2 mole) of β,β-diphenyl-α-cyanoacrylic acid, 30 g. (0.25 mole) of thionyl chloride is added and the solution is refluxed overnight. After cooling, yellow prisms are collected to give 49.5 g., 92% yield of product, m.p. 157°-158° C.

Workup

  1. temperaturethe solution is refluxed overnight
  2. temperatureAfter cooling
  3. customyellow prisms are collected
  4. customto give 49.5 g

Sources & evidence

ORD record
ord-e1ec67767c764bfbbcf95dcf0e62716c
Source dataset
uspto-grants-1983_02
Patent number
US04373060

Reaction notes

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