1,3-Propanedithiol → 1-[4-(3-Mercaptopropylthio)phenyl]-2-dimethylamino-2-benzyl-butan-1-one

HRID 376961

反応式

HRID 376961 の反応式
[CH2:1]([SH:5])[CH2:2][CH2:3][SH:4].C(=O)([O-])[O-].[K+].[K+].F[C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:33])[C:20]([N:30]([CH3:32])[CH3:31])([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:21][CH3:22])=[CH:15][CH:14]=1>CC(N(C)C)=O>[SH:4][CH2:3][CH2:2][CH2:1][S:5][C:13]1[CH:14]=[CH:15][C:16]([C:19](=[O:33])[C:20]([N:30]([CH3:32])[CH3:31])([CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:21][CH3:22])=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 80131,3-PropanedithiolHCID 11430Potassium CarbonateHCID 193605992-Benzyl-2-(dimethylamino)-1-(4-fluorophenyl)butan-1-one

生成物 1

HCID 193606331-[4-(3-Mercaptopropylthio)phenyl]-2-dimethylamino-2-benzyl-butan-1-one

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒2 回

反応条件

温度
50 °C

実験手順

32.5 g (0.3 mol) of 1,3-propanedithiol are dissolved in 50 ml of dry dimethylacetamide, and the solution is heated to about 50° C. together with 13.8 g (0.1 mol) of potassium carbonate. 15.0 g (0.05 mol) of 1-(4-fluorophenyl)-2-dimethylamino-2-benzyl-butan-1-one in 30 ml of dry dimethylacetamide are added dropwise. The suspension is stirred at 50° C. overnight (about 12 hours), then the solid is filtered off. The excess 1,3-propanedithiol and dimethylacetamide are distilled off. To the residue is added toluene, then the precipitate is filtered off. After distilling off the toluene, the residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:7) as an eluent, and an oily product is obtained. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm]: 0.68 (t, 3H), 1.39 (t, 1H), 1.79-1.88 (m, 1H), 1.97-2.11 (m, 3H), 2.36 (s, 6H), 2.69 (q, 2H), 3.12 (t, 2H), 3.19 (s, 2H), 7.15-7.27 (m, 7H), 8.28 (d, 2H).

後処理

  1. filtrationthe solid is filtered off
  2. distillationThe excess 1,3-propanedithiol and dimethylacetamide are distilled off
  3. additionTo the residue is added toluene
  4. filtrationthe precipitate is filtered off
  5. distillationAfter distilling off the toluene
  6. customthe residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:7) as an eluent
  7. customan oily product is obtained

出典と根拠

ORDレコード
ord-cab446e251fe4108813cf01645b94b33
出典データセット
uspto-grants-2000_02
特許番号
US06022906

関連ノート

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