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

HRID 376959
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HRID 376959 반응식
[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
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참가 물질

5

반응물 3

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

생성물 1

HCID 541840361-[3-(Mercaptopropylthio)phenyl]-2-dimethylamino-2-benzyl-propan-1-one

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

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온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e65a01732658481297562396df6567fe
출처 데이터셋
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06022906

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