Hydrogen Sulfide → 10H-phenothiazine-2-carbothioamide

HRID 704165ノート

反応式

HRID 704165 の反応式
C(N(CC)CC([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)C)C.C(N(CC)CC)C.[SH2:32]>N1C=CC=CC=1>[CH:19]1[C:20]2[NH:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[S:14][C:15]=2[CH:16]=[CH:17][C:18]=1[C:21](=[S:32])[NH2:22]

参加物

5

反応物 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 1453650710-(1-Diethylamino-2-propyl)-2-phenothiazinecarbonitrile

生成物 1

HCID 2271158710H-phenothiazine-2-carbothioamide

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
20 °C

実験手順

A solution of 10-[(2RS)-1-diethylamino-2-propyl]2-phenothiazinecarbonitrile (5.66 g) and triethylamine (2.35 cc) in pyridine (113 cc) is treated with hydrogen sulphide for 1 hour and then stirred for 3 days at a temperature in the region of 20° C. The greenish solution obtained is purged with nitrogen, poured into distilled water (500 cc) and extracted with ethyl acetate (2×500 cc). The combined organic phases are washed successively with distilled water (2×200 cc) and with saturated aqueous sodium chloride solution (200 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg, 4 kPa) at 40° C. The residual orange oil (9.1 g) is purified by chromatography on a column (height: 25 cm, diameter: 3 cm) of silica gel (0.04-0.063 mm) with a slight excess pressure of nitrogen (40 kPa), eluting with ethyl acetate (750 cc) and collecting 50-cc fractions. The combined fractions 4 to 10 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 10-[2RS)-1-diethylamino-2-propyl]-2-phenothiazinecarbothioamide (6.2 g) is thereby obtained in the form of an orange oil.

後処理

  1. customThe greenish solution obtained
  2. customis purged with nitrogen
  3. additionpoured
  4. distillationinto distilled water (500 cc)
  5. extractionextracted with ethyl acetate (2×500 cc)
  6. washThe combined organic phases are washed successively with distilled water (2×200 cc) and with saturated aqueous sodium chloride solution (200 cc)
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (30 mm Hg, 4 kPa) at 40° C
  10. customThe residual orange oil (9.1 g) is purified by chromatography on a column (height: 25 cm, diameter: 3 cm) of silica gel (0.04-0.063 mm) with a slight excess pressure of nitrogen (40 kPa)
  11. washeluting with ethyl acetate (750 cc)
  12. customcollecting 50-cc fractions
  13. concentrationThe combined fractions 4 to 10 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

出典と根拠

ORDレコード
ord-8004bd9b1dfd4fc7b039b2ebc2ec9d14
出典データセット
uspto-grants-1991_01
特許番号
US04985419

反応ノート

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