Hydrochloric Acid → 3-Cyano-N,N-dimethylbenzamide
반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](O)=[O:7])#[N:2].S(Cl)(Cl)=O.S(=O)=O.Cl.[CH2:20]([NH:22][CH2:23]C)C.[OH-].[K+]>O.CN(C)C=O.C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([N:22]([CH3:23])[CH3:20])=[O:7])#[N:2]참가 물질
실험 절차
A mixture of 85.22 g of m-cyanobenzoic acid, 400 ml of toluene, 4.48 ml (4.23 g) of N,N-dimethylformamide and 44.4 ml (72.3 g) of thionyl chloride was gently heated on a steam bath for 2 hours with sulfur dioxide and hydrogen chloride being evolved. The reaction solution was cooled in an ice bath and cautiously added portionwise, over one hour, to stirred and cooled solution of 250 ml of 40% aqueous diethylamine and 100 ml of water. At intervals 2-3 ml of concentrated aqueous potassium hydroxide was added. After the addition was complete, the mixture was stirred for several hours, then the layers were separated and the organic layer washed with water. After permitting the organic layer to evaporate to dryness, the residue was recrystallized from 300 ml of ethanol containing charcoal, giving 68.5 g of the desired compound as white crystals, mp 85°-88° C.
후처리
- temperatureThe reaction solution was cooled in an ice bath
- additioncautiously added portionwise, over one hour
- additionAfter the addition
- stirringthe mixture was stirred for several hours
- customthe layers were separated
- washthe organic layer washed with water
- customto evaporate to dryness
- customthe residue was recrystallized from 300 ml of ethanol
- additioncontaining charcoal
출처 및 근거
- ORD 기록
- ord-a731acfb479b4a9b8a500eda84ca313e
- 출처 데이터셋
- uspto-grants-1986_04
- 특허 번호
- US04579848
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