Methyl 4-chloroacetoacetate → HCID 54593430, compound

HRID 572940Notes

Reaction equation

HRID 572940 reaction equation
Cl[CH2:2][C:3](=O)[CH2:4][C:5]([O:7][CH3:8])=[O:6].[CH3:10][NH:11][C:12]([NH2:14])=[S:13]>CO>[CH3:10][NH:11][C:12]1[S:13][CH:2]=[C:3]([CH2:4][C:5]([O:7][CH3:8])=[O:6])[N:14]=1

Participants

4

Reactant 2

HCID 36240Methyl 4-chloroacetoacetateHCID 2723704Methylthiourea

Product 1

HCID 54593430HCID 54593430, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 4-chloro-3-oxobutanoate (1 g, 11.1 mmol) and 1-methylthiourea (1.72 g, 11.43 mmol) in MeOH (5 mL) was heated to 80° C. for 3 hours. The mixture was cooled, ethanol evaporated, and diluted with saturated sodium bicarbonate, and extracted with ethyl acetate. The organic layers were dried over magnesium sulfate and the reaction mixture purified by a standard method to provide methyl 2-(2-(methylamino)thiazol-4-yl)acetate. LC-MS: m/z (M+H)=187.2

Workup

  1. temperatureThe mixture was cooled
  2. customethanol evaporated
  3. additiondiluted with saturated sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layers were dried over magnesium sulfate
  6. customthe reaction mixture purified by a standard method

Sources & evidence

ORD record
ord-b236afa825dc4f01b61bc3c88d3f66cf
Source dataset
uspto-grants-2015_05
Patent number
US09029531B2

Reaction notes

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