Tert-Butyl nitrite → Methyl 5-methyl-1,3-thiazole-4-carboxylate

HRID 577242Notes

Reaction equation

HRID 577242 reaction equation
N(OC(C)(C)C)=O.N[C:9]1[S:10][C:11]([CH3:18])=[C:12]([C:14]([O:16][CH3:17])=[O:15])[N:13]=1>O1CCOCC1>[CH3:18][C:11]1[S:10][CH:9]=[N:13][C:12]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 1132801Methyl 2-amino-5-methyl-1,3-thiazole-4-carboxylate

Product 1

HCID 37818647Methyl 5-methyl-1,3-thiazole-4-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl nitrite (24 mL, 202 mmol) in 1,4-dioxane (180 mL) was added a mixture of methyl 2-amino-5-methyl-1,3-thiazole-4-carboxylate (6.83 g, 40.0 mmol) in 1,4-dioxane (70 mL). The solution was stirred at 60° C. for 1 hour. After cooling to room temperature, the solvent was evaporated. The crude oil was purified by flash chromatography (0-20% EtOAc/hexanes), affording methyl 5-methyl-1,3-thiazole-4-carboxylate (3.95 g, 63%). The product was used for the next step without any further purification.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was evaporated
  3. customThe crude oil was purified by flash chromatography (0-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2c5a002a63aa4a6985e4e47089a58ad7
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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