3-Cyanophenol → O-3-cyanophenyl dimethylthiocarbamate

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[CH3:10][N:11]([CH3:15])[C:12](Cl)=[S:13].[OH-].[K+]>>[CH3:10][N:11]([CH3:15])[C:12](=[S:13])[O:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[CH:3]=1

Participants

Reactant 3

HCID 133943-Cyanophenol

HCID 14797Potassium Hydroxide

HCID 27871Dimethylthiocarbamoyl chloride

Product 1

HCID 14795402O-3-cyanophenyl dimethylthiocarbamate

Procedure

If the procedure described in Preparation XI is followed starting from 15 g (126.10-3 mol) of 3-hydroxybenzonitrile, 17.9 g (145.10-3 mol) of dimethylthiocarbamoyl chloride and 7.4 g (132.10-3 mol) of potassium hydroxide, 29 g (quantitative yield) of the expected product are obtained.

Sources & evidence

ORD record: ord-87ff7015c4e34deb8be2f93ca8168df5
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05101048

Reaction notes

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