Methyl 2-chloro-3-oxopentanoate → Methyl 2-amino-4-ethyl-1,3-thiazole-5-carboxylate

HRID 43449Notes

Reaction equation

HRID 43449 reaction equation
Cl[CH:2]([C:7](=O)[CH2:8][CH3:9])[C:3]([O:5][CH3:6])=[O:4].[NH2:11][C:12]([NH2:14])=[S:13]>C(O)C>[NH2:14][C:12]1[S:13][C:2]([C:3]([O:5][CH3:6])=[O:4])=[C:7]([CH2:8][CH3:9])[N:11]=1

Participants

4

Reactant 2

HCID 545096Methyl 2-chloro-3-oxopentanoateHCID 2723790Thiourea

Product 1

HCID 735005Methyl 2-amino-4-ethyl-1,3-thiazole-5-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2-chloro-3-oxo-pentanoate obtained in Example (22a) (1.91 g, 11.57 mmol) was dissolved in ethanol (50 mL). Thiourea (0.77 g, 10.09 mmol) was added, and the mixture was heated under reflux for 1.5 hours. The reaction solution was concentrated under reduced pressure, diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate solution and brine, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was washed with hexane/ethyl acetate: 5/1 to obtain 1.78 g of the title compound as a pale yellow solid (95%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additiondiluted with ethyl acetate
  5. washwashed with saturated aqueous sodium bicarbonate solution and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentration under reduced pressure
  8. washthe residue was washed with hexane/ethyl acetate

Sources & evidence

ORD record
ord-ea1f7a3df7b74b1c8ff1b2b03700b2c2
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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