Sulfuric Acid → 2-ethylsulfanyl-6-methyl-4-[(3R)-3-methyl-morpholin-4-yl]-benzamide
反応式
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]参加物
3
反応条件
- 温度
- 100 °C
実験手順
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%).
後処理
- 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
出典と根拠
- ORDレコード
- ord-4b4e5bc1496945fb8273814ef70aaef3
- 出典データセット
- uspto-grants-2015_08
- 特許番号
- US09108936B2
反応ノート
読み込み中…