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

HRID 1295828

Reaction equation

HRID 1295828 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 (7-3) 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, thus yielding 0.54 g (48%) of thiazol 5-carboxylic acid methyl ester (7-4).

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-372d32bb21b14d429e50cd966c65ddb0
Source dataset
uspto-grants-2007_07
Patent number
US07244752B2

Linked notes

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