Methyl 2-chloroacetoacetate → methyl 2-amino-4-methylthiazole-5-carboxylate

HRID 560287Notes

Reaction equation

HRID 560287 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[CH3:5][O:6][C:7](=[O:13])[CH:8](Cl)[C:9](=O)[CH3:10]>CCO>[CH3:5][O:6][C:7]([C:8]1[S:3][C:2]([NH2:4])=[N:1][C:9]=1[CH3:10])=[O:13]

Participants

4

Reactant 2

HCID 107332Methyl 2-chloroacetoacetateHCID 2723790Thiourea

Product 1

HCID 713653methyl 2-amino-4-methylthiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of thiourea (59.8 mmol) and 2-chloro-3-oxo-butyric acid methyl ester (59.8 mmol) in EtOH (140 mL) is heated at reflux for 14 h and concentrated in vacuo. Water and aq. NaHCO3 are added and the mixture is extracted several times with EtOAc. The combined organic layers are dried and concentrated in vacuo to give the desired amino-thiazole derivative. LC-MS: tR=0.51 min; [M+H]+=173.0.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 14 h
  3. concentrationconcentrated in vacuo
  4. additionWater and aq. NaHCO3 are added
  5. extractionthe mixture is extracted several times with EtOAc
  6. customThe combined organic layers are dried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9d994200acd7423e964e7b075f97d376
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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