Methanol → 3-(4-Chlorobenzylsulfanyl)-3-(3,4-dimethoxyphenyl)-1-morpholin-4-ylprop-2-en-1-one

HRID 1488946Notes

Reaction equation

HRID 1488946 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][SH:7])=[CH:4][CH:3]=1.CO.Cl[C:13]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=1)=[CH:14][C:15]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:16]>C[O-].[Na+].CN(C)C=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][S:7][C:13]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=2)=[CH:14][C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:16])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 804094-Chlorobenzyl mercaptanHCID 53730792HCID 53730792, compound

Product 1

HCID 540854923-(4-Chlorobenzylsulfanyl)-3-(3,4-dimethoxyphenyl)-1-morpholin-4-ylprop-2-en-1-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 10942334Sodium MethoxideSolvent

Conditions

Temperature
50 °C

Procedure

3.17 g (20 mmol) of 4-chlorobenzylmercaptan are dissolved in 20 ml of methanol containing 3.60 g (20 mmol) of sodium methylate (30%), warmed to 50° C. and then evaporated. A solution of 4.68 g (15 mmol) of 3-chloro-3-(3,4-dimethoxyphenyl)-1-morpholin-4-ylprop-2-en-1-one in 20 ml of dimethylformamide is added. At the end of the exothermic reaction the solution is stirred at 100° C. for 1 hour and the solvent is evaporated. The residue is shaken with toluene/water, the organic phase is washed with water, dried and the reaction product is purified by flash column (150 g of silicagel) chromatography; elution with 1000 ml of toluene containing 10 and 20% of acetone. The fractions with TLC Rf-values 0.45 and 0.38 (toluene/acetone 7:3) are collected and evaporated.

Workup

  1. customevaporated
  2. customAt the end of the exothermic reaction the solution
  3. customthe solvent is evaporated
  4. stirringThe residue is shaken with toluene/water
  5. washthe organic phase is washed with water
  6. customdried
  7. customthe reaction product is purified by flash column (150 g of silicagel) chromatography
  8. washelution with 1000 ml of toluene containing 10 and 20% of acetone
  9. customThe fractions with TLC Rf-values 0.45 and 0.38 (toluene/acetone 7:3) are collected
  10. customevaporated

Sources & evidence

ORD record
ord-df740e024cfb4337a64c6cad22c953f9
Source dataset
uspto-grants-1997_10
Patent number
US05677303

Reaction notes

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