Acetic Acid → 10-[(2RS)-1-diethylamino-2-propyl]-N-(2-methylpropyl)-2-phenothiazinecarboxamide
反応式
[CH2:1]([N:3]([CH2:28][CH3:29])[CH2:4][CH:5]([N:7]1[C:20]2[CH:19]=[C:18]([C:21](=S)[NH:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH:17]=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:6])[CH3:2].C(O)(=[O:32])C>C(OCC)(=O)C>[CH2:1]([N:3]([CH2:28][CH3:29])[CH2:4][CH:5]([N:7]1[C:20]2[CH:19]=[C:18]([C:21]([NH:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:32])[CH:17]=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:6])[CH3:2]参加物
4
反応条件
- 温度
- 25 °C
実験手順
A solution of mercuric acetate (0.84 g) in glacial acetic acid (13 cc) is added dropwise during a period of 10 minutes to a solution of 10-[(2RS)-1-diethylamino-2-propyl]-N-(2-methylpropyl)-2-phenothiazinecarbothioamide (1.12 g) in glacial acetic acid (13 cc). The reaction mixture is stirred for 90 minutes at 25° C. and then filtered on sintered glass covered with celite. The celite is washed with acetic acid (2 cc) and the combined filtrates are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give a residue which is then diluted in ethyl acetate (50 cc). The organic phase is washed with normal caustic soda solution (25 cc) and distilled water (3×25 cc) and then with brine (1×25 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give a residue which is purified by chromatography on a column (height: 17.2 cm; diameter: 2.4 cm) of silica gel (0.04-0.06 mm) with a slight excess pressure of nitrogen (40 kPa), eluting with a 50:50 (by volume) mixture (1 liter) of cyclohexane and ethylacetate, collecting 60-cc fractions. Fractions 4 to 14 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give 10-[(2RS)-1-diethylamino-2-propyl]-N-(2-methylpropyl)-2-phenothiazinecarboxamide (0.83 g).