Acetyl chloride → Methyl 2-phenyl-1,3-thiazole-5-carboxylate

HRID 2256810Notes

Reaction equation

HRID 2256810 reaction equation
[C:1](Cl)(=O)C.[C:5]1([C:11]2[S:12][C:13]([C:16]([OH:18])=[O:17])=[CH:14][N:15]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CO>[C:5]1([C:11]2[S:12][C:13]([C:16]([O:18][CH3:1])=[O:17])=[CH:14][N:15]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 1390872-Phenyl-5-carboxythiazole

Product 1

HCID 18913489Methyl 2-phenyl-1,3-thiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.5 ml of acetyl chloride were added to a solution of 4.77 g of the acid of Stage B in 160 ml of methanol, and the mixture was refluxed for 18 hours. After evaporating to dryness under reduced pressure, the residue was taken up in ethyl acetate. The mixture was filtered and concentrated to a reduced volume. The crystals were separated off and the mother liquors were washed with sodium hydroxide. Extraction was carried out with ethyl acetate, followed by washing with water and evaporating to dryness. The 2 crystallized fractions were combined to obtain 4.54 g of the desired product melting at 108° C.

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. customAfter evaporating to dryness under reduced pressure
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated to a reduced volume
  5. customThe crystals were separated off
  6. washthe mother liquors were washed with sodium hydroxide
  7. extractionExtraction
  8. washby washing with water
  9. customevaporating to dryness

Sources & evidence

ORD record
ord-272f3d0548564e16b3427e213d9500ae
Source dataset
uspto-grants-1997_08
Patent number
US05656607

Reaction notes

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