Dimethylformamide → 3-Methoxy-4-methylbenzonitrile
Reaction equation
ClS([N:5]=C=O)(=O)=O.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[CH3:19])[C:13](O)=O.CN(C)C=O>ClCCl>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[CH3:19])[C:13]#[N:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of chlorosulphonyl isocyanate (5.35 ml.) in dichloromethane (3 ml.) was added over 45 minutes to a stirred suspension of 3-methoxy-4-methylbenzoic acid (9.97 g.) in dichloromethane (18 ml.) at reflux under an atomosphere of nitrogen. The resulting bright-red homogeneous solution was heated under reflux for 45 minutes, chilled in an ice-bath, and treated dropwise with N,N-dimethylformamide (9.5 ml.), over 15 minutes. After stirring for 30 minutes at 0° C., the orange solution was poured onto ice. The organic layer was separated, washed with water (5×20 ml.), dried (MgSO4) and evaporated. The residue was purified by preparative HPLC (SiO2, 10:90 v/v hexane: toluene) to give 3-methoxy-4-methylbenzonitrile (5.28 g., 60%) as a white solid, m.p. 51°-52.5° C.
Workup
- temperatureat reflux under an atomosphere of nitrogen
- temperatureThe resulting bright-red homogeneous solution was heated
- temperatureunder reflux for 45 minutes
- temperaturechilled in an ice-bath
- additionthe orange solution was poured onto ice
- customThe organic layer was separated
- washwashed with water (5×20 ml.)
- dry with materialdried (MgSO4)
- customevaporated
- customThe residue was purified by preparative HPLC (SiO2, 10:90 v/v hexane: toluene)
Sources & evidence
- ORD record
- ord-59e335b90c164165a6962fabc8a3c3c4
- Source dataset
- uspto-grants-1996_12
- Patent number
- US05583152
Reaction notes
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