Methanol → HCID 54724774, compound

HRID 2216400Notes

Reaction equation

HRID 2216400 reaction equation
[Na].CO.[C:4]([O:8][CH3:9])(=[O:7])[CH2:5][SH:6].Cl[C:11]1[C:16]([C:17](OCC)=[O:18])=[CH:15][CH:14]=[C:13]([CH:22]([CH3:24])[CH3:23])[N:12]=1>CN(C)C=O.O>[CH3:9][O:8][C:4]([C:5]1[S:6][C:11]2=[N:12][C:13]([CH:22]([CH3:23])[CH3:24])=[CH:14][CH:15]=[C:16]2[C:17]=1[OH:18])=[O:7]

Participants

7

Reactant 4

HCID 887MethanolHCID 16907Methyl ThioglycolateHCID 5360545SodiumHCID 21942344Ethyl 2-chloro-6-(propan-2-yl)pyridine-3-carboxylate

Product 1

HCID 54724774HCID 54724774, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under ice-cooling, metal sodium (6.9 g) was added to methanol (70 ml)-and methyl thioglycolate (32 g) was added with stirring. Ethyl 2-chloro-6-isopropylpyridine-3-carboxylate (42 g) synthesized according to U.S. Pat. No. 5,001,137 (Mar. 19, 1991) was dissolved in dimethylformamide (170 ml) and the mixture was stirred at room temperature for 2 hr. The reaction mixture was treated with water, and the organic layer was extracted with ethyl acetate, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained crystals were recrystallized from water-containing methanol to give the title compound (20.9 g). melting point: 80-81° C.

Workup

  1. temperatureUnder ice-cooling
  2. additionwas added
  3. stirringthe mixture was stirred at room temperature for 2 hr
  4. extractionthe organic layer was extracted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customThe obtained crystals were recrystallized from water-
  9. additioncontaining methanol

Sources & evidence

ORD record
ord-09dd42b327c647939bde6cc37a318ae4
Source dataset
uspto-grants-2006_09
Patent number
US07112594B2

Reaction notes

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