Isoamyl Nitrite → Methyl 1,3-thiazole-5-carboxylate

HRID 1437446

Reaction equation

HRID 1437446 reaction equation
N(OCCC(C)C)=O.[CH3:9][O:10][C:11]([C:13]1[S:17][C:16](N)=[N:15][CH:14]=1)=[O:12].C(OCC)(=O)C>O1CCOCC1>[CH3:9][O:10][C:11]([C:13]1[S:17][CH:16]=[N:15][CH:14]=1)=[O:12]

Participants

5

Reactant 3

HCID 8053Isoamyl NitriteHCID 8857Ethyl AcetateHCID 238005Methyl 2-aminothiazole-5-carboxylate

Product 1

HCID 331117Methyl 1,3-thiazole-5-carboxylateYield 48.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

The mixture of 2.15 g of isoamyl nitrite and 10 ml of dioxane was stirred at 80° C. under a nitrogen atmosphere. A solution of 1.23 g of 2-aminothiazole-5-carboxylic acid methyl ester (8-3) in 20 ml of dioxane was added drop wise. The mixture was refluxed for 2 hours. After cooling to room temperature 30 ml of ethyl acetate was added. The mixture was washed with brine and dried and the solvent evaporated under reduced pressure. The crude product is purified on silica, yielding 0.54 g (48%) of thiazol 5-carboxylic acid methyl ester (84).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. additionwas added
  3. washThe mixture was washed with brine
  4. customdried
  5. customthe solvent evaporated under reduced pressure
  6. customThe crude product is purified on silica

Sources & evidence

ORD record
ord-0d4224bd8a6e48b093f211d471b80dc4
Source dataset
uspto-grants-2009_11
Patent number
US07622490B2

Linked notes

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