Sulfuric Acid → 2-ethylsulfanyl-6-methyl-4-[(3R)-3-methyl-morpholin-4-yl]-benzamide
반응식
S(=O)(=O)(O)[OH:2].[CH2:6]([S:8][C:9]1[CH:16]=[C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][C@H:18]2[CH3:23])[CH:14]=[C:13]([CH3:24])[C:10]=1[C:11]#[N:12])[CH3:7]>>[CH2:6]([S:8][C:9]1[CH:16]=[C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][C@H:18]2[CH3:23])[CH:14]=[C:13]([CH3:24])[C:10]=1[C:11]([NH2:12])=[O:2])[CH3:7]참가 물질
3
반응 조건
- 온도
- 100 °C
실험 절차
Concentrated sulfuric acid (5 ml) is added to 2-ethylsulfanyl-6-methyl-4-[(3R)-3-methyl-morpholin-4-yl]-benzonitrile (0.11 g, 0.40 mmol) at RT and the resulting mixture is heated at 100° C. for 4 h. Upon completion (monitored by TLC), the reaction is slowly quenched with ice at 0° C. The mixture is basified with aqueous ammonia (pH=10). The aqueous part is extracted with ethyl acetate (3×10 ml). The combined organic layers are washed with water (10 ml), brine (10 ml), dried over anhydrous sodium sulfate and evaporated to get 2-ethylsulfanyl-6-methyl-4-[(3R)-3-methyl-morpholin-4-yl]-benzamide which is used in the next step without further purification (0.075 g, 0.26 mmol, 55%).
후처리
- customUpon completion (monitored by TLC), the reaction is slowly quenched with ice at 0° C
- extractionThe aqueous part is extracted with ethyl acetate (3×10 ml)
- washThe combined organic layers are washed with water (10 ml), brine (10 ml)
- dry with materialdried over anhydrous sodium sulfate
- customevaporated
출처 및 근거
- ORD 기록
- ord-4b4e5bc1496945fb8273814ef70aaef3
- 출처 데이터셋
- uspto-grants-2015_08
- 특허 번호
- US09108936B2
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