Dimethylcarbamoyl Chloride → 4-Dimethylcarbamoyloxy-2,5-dimethylphenyl methyl sulphide
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[C:5]([CH3:10])=[CH:4][C:3]=1[OH:11].[CH3:12][N:13]([CH3:17])[C:14](Cl)=[O:15]>N1C=CC=CC=1>[CH3:9][S:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([O:11][C:14](=[O:15])[N:13]([CH3:17])[CH3:12])=[CH:4][C:5]=1[CH3:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 25.2 g 2,5-dimethyl-4-(methylthio)phenol and 20.3 ml dimethylcarbamoyl chloride in 70 ml dry pyridine was heated for 24 hours at 100° C. Addition to excess of ice-cold dilute hydrochloric acid gave an oil. The oil product was extracted into ether and washed three times with cold dilute sodium hydroxide and once with water, dried, and the ether removed by evaporation to give 4-dimethylcarbamoyloxy-2,5-dimethylphenyl methyl sulphide, boiling point 146° C. at 0.6 mm to 150° C. to 0.9 mm.
Workup
- additionAddition to excess of ice-cold dilute hydrochloric acid
- customgave an oil
- extractionThe oil product was extracted into ether
- washwashed three times with cold dilute sodium hydroxide
- dry with materialonce with water, dried
- customthe ether removed by evaporation
Sources & evidence
- ORD record
- ord-7230bcee4b094bab8a059f5deb486c74
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04221582
Reaction notes
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