Methanol → Methyl 3-phenylmethylthiopyridine-4-carboxylate

HRID 35538Notes

Reaction equation

HRID 35538 reaction equation
[C:1]1([CH2:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[C:14]([OH:16])=[S:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH3:22]O>COC(OC)(C)C>[C:1]1([CH2:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[C:14]([O:16][CH3:22])=[S:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178526144HCID 178526144, compound

Product 1

HCID 86742398Methyl 3-phenylmethylthiopyridine-4-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of 5.1 g (20 mmol) of 3-phenylmethylthiopyridine-4-carboxylic acid in 150 mL of methanol, 1.6 mL of 2,2-dimethoxypropane, and 5 mL of sulfuric acid was heated at reflux for 18 hours. The solution was cooled, concentrated to 25 mL, then partitioned between ether and sodium bicarbonate solution. The ether layer was washed with sodium bicarbonate solution, then brine, then dried and concentrated to afford 5.0 g (96%) of white crystals, m.p. 79°-80° C.

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe solution was cooled
  3. concentrationconcentrated to 25 mL
  4. custompartitioned between ether and sodium bicarbonate solution
  5. washThe ether layer was washed with sodium bicarbonate solution
  6. dry with materialbrine, then dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9626ea8265e140e9919731623ca102ec
Source dataset
uspto-grants-1988_08
Patent number
US04767766

Reaction notes

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