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

HRID 376959Notes

Reaction equation

HRID 376959 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
50 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-e65a01732658481297562396df6567fe
Source dataset
uspto-grants-2000_02
Patent number
US06022906

Reaction notes

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