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

HRID 630283Notes

Reaction equation

HRID 630283 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-9e1cde965b22496c81cf1973702c94f3
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

Loading…