Water → 5-Acetyl-4-methylthiazole

HRID 648604

Reaction equation

HRID 648604 reaction equation
[C:1]([C:4]1[S:8][C:7](N)=[N:6][C:5]=1[CH3:10])(=[O:3])[CH3:2].C(ON=O)CC(C)C.C(OCC)(=O)C.O>O1CCCC1.CN(C)C=O>[C:1]([C:4]1[S:8][CH:7]=[N:6][C:5]=1[CH3:10])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8053Isoamyl NitriteHCID 8857Ethyl AcetateHCID 7208825-Acetyl-2-amino-4-methylthiazole

Product 1

HCID 1622925-Acetyl-4-methylthiazoleYield 54.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-acetyl-2-amino-4-methylthiazole (15.6 g) in a mixture of tetrahydrofuran (200 ml) and dimethylformamide (50 ml) was added dropwise isoamylnitrite (14.6 g) at 50° C. to 55° C. with stirring and the mixture was stirred at 55° C. to 60° C. for 4 hours. The reaction mixture was poured into a mixture of ethyl acetate and water with stirring. The separated organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was subjected to column chromatography on silica gel and eluted with a mixture of diisopropyl ether and ethyl acetate (1:1). The fractions containing the desired compound were combined and evaporated in vacuo to give 5-acetyl-4-methylthiazole (7.7 g) as an oil.

Workup

  1. stirringthe mixture was stirred at 55° C. to 60° C. for 4 hours
  2. stirringwith stirring
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. washeluted with a mixture of diisopropyl ether and ethyl acetate (1:1)
  7. additionThe fractions containing the desired compound
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-76972a5b2f2349c9838aa65b3ee7faa4
Source dataset
uspto-grants-1988_04
Patent number
US04735957

Linked notes

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