Methyl iodide → 10-[(2RS)-1-(N-ethyl-N-methylamino)-2-propyl]-2-phenothiazinecarbonitrile

HRID 728711ノート

反応式

HRID 728711 の反応式
[CH2:1]([NH:3][CH2:4][CH:5]([N:7]1[C:20]2[CH:19]=[C:18]([C:21]#[N:22])[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:23](=O)([O-])[O-].[Na+].[Na+].IC>CN(C)C=O>[CH2:1]([N:3]([CH2:4][CH:5]([N:7]1[C:20]2[CH:19]=[C:18]([C:21]#[N:22])[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])[CH3:23])[CH3:2]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 14536548HCID 14536548、化合物

生成物 1

HCID 1453655310-[(2RS)-1-(N-ethyl-N-methylamino)-2-propyl]-2-phenothiazinecarbonitrile収率 65.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

A mixture of 10-[(2RS)-1-ethylamino-2-propyl]-2-phenothiazinecarbonitrile (4.4 g), sodium carbonate (2.25 g) and iodomethane (0.9 cc in dimethylformamide (60 cc) is heated for 6 hours to a temperature in the region of 150° C. The reaction mixture is then concentrated to dryness under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C. and the residue is taken up with distilled water (100 cc) and extracted with ethyl acetate (2×100 cc). The combined organic phases are extracted with N aqueous hydrochloric acid solution (2×50 cc). The combined aqueous phases are alkalinized with sodium hydroxide (d =1.33) to pH 13 and extracted with ethyl acetate (2×100 cc). The combined organic phases are washed successively with distilled water (50 cc) and with saturated aqueous sodium chloride solution (50 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 10-[(2RS)-1-(N-Ethyl-N-methylamino)-2-propyl]-2-phenothiazinecarbonitrile (3 g) is thereby obtained in the form of an orange oil. PG,47

後処理

  1. concentrationThe reaction mixture is then concentrated to dryness under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C.
  2. extractionextracted with ethyl acetate (2×100 cc)
  3. extractionThe combined organic phases are extracted with N aqueous hydrochloric acid solution (2×50 cc)
  4. extractionextracted with ethyl acetate (2×100 cc)
  5. washThe combined organic phases are washed successively with distilled water (50 cc) and with saturated aqueous sodium chloride solution (50 cc)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

出典と根拠

ORDレコード
ord-f0f6fa824bc84f62b4c205656d336e9b
出典データセット
uspto-grants-1991_09
特許番号
US05049669

反応ノート

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