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

HRID 376961

반응식

HRID 376961 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: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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cab446e251fe4108813cf01645b94b33
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06022906

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