Hydrochloric Acid → 2,6-Dimethoxybenzoyl isocyanate
Reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:4]=1[C:5]([NH2:7])=[O:6].C1(C)C=CC=CC=1.C(Cl)(=O)[C:22](Cl)=[O:23].Cl>O>[CH3:13][O:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[C:4]=1[C:5]([N:7]=[C:22]=[O:23])=[O:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A 167 g. portion of 2,6-dimethoxybenzamide was slurried in 2 l. of toluene under a nitrogen atmosphere. To this solution was added 145 g. of oxalyl chloride over a one hour period. The solution was heated to 60° C. and maintained at this temperature overnight. HCl was allowed to escape while attempting to prevent water from condensing and going into the reaction mixture. Nitrogen was bubbled subsurface through a gas inlet tube while heating the reaction mixture at reflux (about 110° C.) for 11/2 hours. As stirring continued, the mixture was allowed to come to about 30° C. The solution was filtered through infusorial earth while maintaining a nitrogen atmosphere and the solvent was removed in vacuo. Yield 185 g. (97%). The oil was then stored under nitrogen.
Workup
- additionTo this solution was added 145 g
- temperaturemaintained at this temperature overnight
- customfrom condensing
- customNitrogen was bubbled subsurface through a gas inlet tube
- temperaturewhile heating the reaction mixture
- temperatureat reflux (about 110° C.) for 11/2 hours
- customto come to about 30° C
- filtrationThe solution was filtered through infusorial earth
- temperaturewhile maintaining a nitrogen atmosphere
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-9aba7ccf714c4f3e93da40c9f591e2ac
- Source dataset
- uspto-grants-1984_06
- Patent number
- US04452631
Reaction notes
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