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

HRID 376959
ノート
印刷プレビュー

反応式

HRID 376959 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:32])[C:20]([N:29]([CH3:31])[CH3:30])([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:21])=[CH:15][CH:14]=1>CC(N(C)C)=O>[SH:4][CH2:3][CH2:2][CH2:1][S:5][C:18]1[CH:17]=[C:16]([C:19](=[O:32])[C:20]([N:29]([CH3:30])[CH3:31])([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH3:21])[CH:15]=[CH:14][CH:13]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 80131,3-PropanedithiolHCID 11430Potassium CarbonateHCID 187550662-(Dimethylamino)-1-(4-fluorophenyl)-2-methyl-3-phenylpropan-1-one

生成物 1

HCID 541840361-[3-(Mercaptopropylthio)phenyl]-2-dimethylamino-2-benzyl-propan-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

22.8 g (0.21 mol) of 1,3-propanedithiol is dissolved in 50 ml of dry dimethylacetamide, 4.8 g of potassium carbonate are added and the mixture is heated to about 50° C. 10.0 g of 1-(4-fluorophenyl) 2-dimethylamino-2-benzyl-propan-1-one in 50 ml of dry dimethylacetamide are added dropwise. The suspension is stirred at 50° C. for 12 h, the solid is filtered off. The excess 1,3-propandithiol and dimethylacetamide are distilled off. To the residue toulene is added and the resulting precipitate is filtered off. After the toluene is distilled off, the residue is purified by column chromatography on silica gel with ethyl acetate-hexane (1:9) as eluent. The structure is confirmed by the 1H-NMR-spectrum, measured in CDCl3. The signals (δ in ppm) are 1.16 (s,3H), 1.40 (t, 1H), 2.02 (m,2H), 2.34 (s,6H), 2.71 (q,2H), 2.96 (d, 1H), 3.14 (t,2H), 3.68 (d,1H), 6.88 (m,2H), 7.12 (m,3H), 7.29 (d,2H), 8.44 (d,2H).

後処理

  1. filtrationthe solid is filtered off
  2. distillationThe excess 1,3-propandithiol and dimethylacetamide are distilled off
  3. additionTo the residue toulene is added
  4. filtrationthe resulting precipitate is filtered off
  5. distillationAfter the toluene is distilled off
  6. customthe residue is purified by column chromatography on silica gel with ethyl acetate-hexane (1:9) as eluent

出典と根拠

ORDレコード
ord-e65a01732658481297562396df6567fe
出典データセット
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06022906

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート