HCID 86747405, compound → HCID 19736704, compound

HRID 326309Notes

Reaction equation

HRID 326309 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([C:11](=[O:13])[CH3:12])=[C:5]([SH:14])[CH:4]=1>CO>[CH3:10][O:9][C:7]1[C:6]2[C:11](=[O:13])[CH2:12][C:3]3([S:14][C:5]=2[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]3

Participants

3

Reactant 1

HCID 86747405HCID 86747405, compound

Product 1

HCID 19736704HCID 19736704, compoundYield 143.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (4',6'-dimethoxy-2'-mercaptophenyl) ethanone (prepared in Preparation 77) (0.53 g, 2.5 mmol) and cyclohexanonepyrrolidine enamine (0.57 g, 3.73 mmol) in dry methanol (8 ml) is heated to reflux for 3 hours under nitrogen gas. The solvent is removed by distillation and the residue is dissolved in diethyl ether. The solution is washed with dilute hydrochloric acid and then saturated brine, dried, and the solvent is removed. The residue is placed on a silica gel column and eluted with a mixture of ethyl acetate and dichloromethane (1:9). The starting material (0.142 g, 26%) and the title compound (crystalline solid, 0.526 g, 71.9%) are obtained, successively. Recrystallization from diethyl ether gives the title compound having a melting point of 104°-105° C.

Workup

  1. temperatureto reflux for 3 hours under nitrogen gas
  2. customThe solvent is removed by distillation
  3. dissolutionthe residue is dissolved in diethyl ether
  4. washThe solution is washed with dilute hydrochloric acid
  5. dry with materialsaturated brine, dried
  6. customthe solvent is removed
  7. washeluted with a mixture of ethyl acetate and dichloromethane (1:9)

Sources & evidence

ORD record
ord-301b8d35006b4a338b51ce797e8b9904
Source dataset
uspto-grants-1993_12
Patent number
US05268386

Reaction notes

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