Water → Methyl 2-methoxy-5-phenylthiazole-4-carboxylate

HRID 1154754Notes

Reaction equation

HRID 1154754 reaction equation
Cl[C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1.[CH3:17][O-:18].[Na+].O>CO>[CH3:17][O:18][C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 12821997Methyl 2-chloro-5-phenyl-4-thiazolecarboxylate

Product 1

HCID 12821998Methyl 2-methoxy-5-phenylthiazole-4-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Under a static N2 atm, a stirred solution of the compound of Example 2 (8.14 g, 32 mol) in 100 ml of methanol was treated dropwise with 7.6 g of 25% sodium methoxide in methanol. After stirring at ambient temperature for 24 hr, the mixture was added to H2O and extracted twice with ether. The ether layer was washed with H2O, dried over MgSO4 and concentrated in vacuo to yield a white solid which was recrystallized from methylcyclohexane to yield 5.5 g of methyl 2-methoxy-5-phenyl-4-thiazolecarboxylate as a white solid, m.p. 86°-88° C., yield 70%.

Workup

  1. extractionextracted twice with ether
  2. washThe ether layer was washed with H2O
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto yield a white solid which
  6. customwas recrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-5f6a3c5eff844e1baa0a0ffcf4eb85ae
Source dataset
uspto-grants-1981_11
Patent number
US04298375

Reaction notes

Loading…