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

HRID 2391166Notes

Reaction equation

HRID 2391166 reaction equation
N[C:2]1[S:3][C:4]([CH3:11])=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1.N(OC(C)(C)C)=O>O1CCCC1.O>[CH3:11][C:4]1[S:3][CH:2]=[N:6][C:5]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

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 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 2-amino-5-methyl-1,3-thiazole-4-carboxylate (2.15 g, 12.5 mmol) in tetrahydrofuran (60 mL) was slowly added tert-butyl nitrite (2.23 mL, 18.7 mmol) with stirring at 50° C., and the mixture was stirred at 60° C. for 2 hr. The mixture was diluted with water (100 mL), and extracted with ethyl acetate (100 mL×2). The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→0/100) to give the title compound (1.17 g, yield 60%).

Workup

  1. stirringthe mixture was stirred at 60° C. for 2 hr
  2. extractionextracted with ethyl acetate (100 mL×2)
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→0/100)

Sources & evidence

ORD record
ord-4fb40864a0f74013a61610138ffc7308
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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