Thionyl Chloride → HCID 19976091, compound

HRID 274917Notes

Reaction equation

HRID 274917 reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][C:8]=1[CH:9]=[N:10]O>C1C=CC=CC=1>[CH3:5][O:6][C:7]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][C:8]=1[C:9]#[N:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 73668580HCID 73668580, compound

Product 1

HCID 19976091HCID 19976091, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Thionyl chloride (11.9 ml, 163 mmol) was added under a nitrogen atmosphere to a suspension of 2-methoxy-5-phenoxybenzaldehyde oxime (3.96 g, 16.3 mmol) in 75 ml of benzene. There was a slight exotherm and the mixture turned yellow. The reaction was heated to reflux temperature over 1 hour and at reflux temperature for an additional hour. The solvent and excess thionyl chloride were removed under reduced pressure to give 2-methoxy-5-phenoxybenzonitrile as a light tan crystalline solid (3.66 g, 100% ), mp 88°-89° C.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux temperature over 1 hour
  3. temperatureat reflux temperature for an additional hour
  4. customThe solvent and excess thionyl chloride were removed under reduced pressure

Sources & evidence

ORD record
ord-93355687e2e24837986e8dc35407c53e
Source dataset
uspto-grants-1995_02
Patent number
US05391571

Reaction notes

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