Thionyl Chloride → 2-Cyano-3-phenylprop-2-enoyl chloride

HRID 2395529Notes

Reaction equation

HRID 2395529 reaction equation
[C:1]([C:3](=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4](O)=[O:5])#[N:2].S(Cl)([Cl:16])=O>C1C=CC=CC=1>[C:1]([C:3](=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]([Cl:16])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 705342-Cyano-3-phenylprop-2-enoic acid

Product 1

HCID 540043722-Cyano-3-phenylprop-2-enoyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

100 ml of benzene was added to 17.3 grams of α-cyanocinnamic acid. 12 ml of thionyl chloride was added dropwise slowly thereto at ambient temperature. The temperature was elevated to 70° C. and the heating was continued until foaming ceased. Benzene and thionyl chloride were distilled off and the residue was dried thoroughly under reduced pressure.

Workup

  1. customat ambient temperature
  2. customwas elevated to 70° C.
  3. distillationBenzene and thionyl chloride were distilled off
  4. customthe residue was dried thoroughly under reduced pressure

Sources & evidence

ORD record
ord-a4bd5f6154344f4ba343b843c72f7e16
Source dataset
uspto-grants-1996_02
Patent number
US05489387

Reaction notes

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