Water → HCID 19360625, compound

HRID 376957Notes

Reaction equation

HRID 376957 reaction equation
SC1C=CC(S[C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:25])[C:16]([CH3:24])([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH3:17])=[CH:11][CH:10]=2)=CC=1.[SH:26][CH2:27][CH:28]([OH:33])[CH:29]([OH:32])[CH2:30][SH:31].C(=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[OH:33][CH:28]([CH:29]([OH:32])[CH2:30][SH:31])[CH2:27][S:26][C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:25])[C:16]([CH3:17])([N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[CH3:24])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 190011,4-Dimercapto-2,3-butanediolHCID 19360595HCID 19360595, compound

Product 1

HCID 19360625HCID 19360625, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1.0 g (4.0 mmol) of 1-[4-(4-mercaptophenylthio)phenyl]-2-methyl-2-morpholine-4-yl-propane-1-one and 1.37 g (8.9 mmol) of 1,4-dimercapto-2,3-butanediol are dissolved in 50 ml of dry dimethylacetamide, 1.10 g (8.0 mmol) of potassium carbonate are added and the mixture is stirred for 17 h. The resulting suspension is poured into water and extracted with ethyl acetate, the combined organic phases are washed with water. The solvent is distilled off and the residual oil is purified by column chromatography on silica gel with ethanol-methylene chloride (5:95) as eluent. The structure is confirmed by the 1H-NMR-spectrum, measured in CDCl3. The signals (δ in ppm) are 1.31 (s,6H), 1.55 (t,1 H), 2.57 (m,4H), 2.75 (m, 1H), 3.24 (m,5H), 3.70 (m,5H), 4.18 (s,1H), 7.53 (d,2H), 8.49 (d,2H).

Workup

  1. extractionextracted with ethyl acetate
  2. washthe combined organic phases are washed with water
  3. distillationThe solvent is distilled off
  4. customthe residual oil is purified by column chromatography on silica gel with ethanol-methylene chloride (5:95) as eluent

Sources & evidence

ORD record
ord-eb7ef072de36473d893a88f8212b3eab
Source dataset
uspto-grants-2000_02
Patent number
US06022906

Reaction notes

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