Methanol → HCID 86599618, compound

HRID 2222207Notes

Reaction equation

HRID 2222207 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH2:11])=[S:10])=[CH:4][C:3]=1[O:12][CH3:13].[CH3:14][OH:15]>>[CH3:14][O:15][C:3]([C:2]1[N:11]=[C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:12][CH3:13])[CH:4]=2)[S:10][C:7]=1[CH3:6])=[O:12]

Participants

3

Reactant 2

HCID 887MethanolHCID 86056613N-(4-Chloro-3-methoxyphenyl)thiourea

Product 1

HCID 86599618HCID 86599618, compoundYield 50%

Procedure

A mixture of 8.7 g (40.1 mmol) 1-(4-chloro-3-methoxyphenyl)-thiourea and 7.5 g (0.44 mmol) α-methylchloropyruvate (J. Chem Soc. Perkin 1, 1982, 2, 159) in 140 ml methanol was heated under reflux for 5 h, cooled to room temperature and volatiles were removed. The residue was dissolved in dichloromethane and washed successively with 25% aq. ammonia and water. Water phases were extracted thrice with dichloromethane, the organic phases were pooled, dried with MgSO4 and the solvent removed in vacuo. The residue was purified by chromatography on silica gel with heptane/ethyl acetate (1:2) to give 6.2 g (50%) of the title compound as colorless solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 h
  3. customvolatiles were removed
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed successively with 25% aq. ammonia and water
  6. extractionWater phases were extracted thrice with dichloromethane
  7. dry with materialdried with MgSO4
  8. customthe solvent removed in vacuo
  9. customThe residue was purified by chromatography on silica gel with heptane/ethyl acetate (1:2)

Sources & evidence

ORD record
ord-4d28973a8afb41eb9513d0a5cf08d46c
Source dataset
uspto-grants-2008_05
Patent number
US07371751B2

Reaction notes

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