HCID 766578, compound → Ethyl 5-methylthiazole-4-carboxylate

HRID 2427266Notes

Reaction equation

HRID 2427266 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](N)[S:9][C:10]=1[CH3:11])=[O:5])[CH3:2]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][S:9][C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 766578HCID 766578, compound

Product 1

HCID 12300671Ethyl 5-methylthiazole-4-carboxylateYield 68.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 3-neck round bottom flask mix 2-amino-5-methyl-thiazole-4-carboxylic acid ethyl ester (62.9 g, 338 mmol) and THF (630 mL). Heat to reflux and treat the reaction mixture with isoamyl nitrile (52.6 g, 60.1 mL, 449 mmol) dropwise. Upon completion of the addition, stir the reaction at reflux for 1 h, then concentrate the reaction mixture by rotavap (hi-vac) to give 70 g crude product as a thick orange oil. Purify on silica gel (400 g, 20-45% EtOAc/hexanes) to afford 39.47 g (68%) of the title compound as a yellow solid. LC-ES/MS m/z 172 (M+1), TR=1.5 min.

Workup

  1. temperatureHeat
  2. temperatureto reflux
  3. additionUpon completion of the addition
  4. customthe reaction
  5. temperatureat reflux for 1 h
  6. concentrationconcentrate the reaction mixture by rotavap (hi-vac)
  7. customto give 70 g crude product as a thick orange oil
  8. customPurify on silica gel (400 g, 20-45% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b5c31610baad4facb5551c2f4149a3cc
Source dataset
uspto-grants-2011_06
Patent number
US07968587B2

Reaction notes

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