Ethyl 2-chloroacetoacetate → HCID 4820961, compound

HRID 439286Notes

Reaction equation

HRID 439286 reaction equation
[CH3:1][NH:2][C:3]([NH2:5])=[S:4].Cl[CH:7]([C:13]([CH3:15])=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9]>ClCCCl>[CH3:1][NH:2][C:3]1[S:4][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:13]([CH3:15])[N:5]=1

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 2723704Methylthiourea

Product 1

HCID 4820961HCID 4820961, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3.6g of methyl thiourea and 7.9g of ethyl 2-chloroacetoacetate were added to 100ml of 1,2-dichloroethane and the mixture was stirred under reflux for 10 hours. After removing the solvent under reduced pressure, 10% aqueous sodium hydroxide solution was added thereto to recrystallize the resulting product which was then filtered to obtain 7.8g (Yield 96%) of ethyl 2-methylamino-4-methyl-thiazole-5-carboxylate as a pale yellow solid. The obtained solid product was dissolved in 60ml of a mixed solvent of methanol-distilled water (v/v=3/1) containing 1.8g of sodium hydroxide. The reaction mixture was stirred under reflux for 8 hours, evaporated under reduced pressure to remove methanol and then adjusted to pH 2 to 3 by adding 10% aqueous hydrochloric acid solution to precipitate the white solid. The precipitated solid product was filtered, washed with water and diethylether and then dried to obtain 6.0g (Yield 90%) of the title compound as a white solid.

Workup

  1. temperatureunder reflux for 10 hours
  2. customAfter removing the solvent under reduced pressure, 10% aqueous sodium hydroxide solution
  3. additionwas added
  4. customto recrystallize the resulting product which
  5. filtrationwas then filtered

Sources & evidence

ORD record
ord-05d8aaaa75be40d6944c037a886d536b
Source dataset
uspto-grants-1996_05
Patent number
US05514643

Reaction notes

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