Reaction #1509580

ord-757bce8d5c33420980255c8d8a6e7596

Reaction equation

NC(N)=S
thiourea
CCOC(=O)C(Br)C(=O)C(C)C
Ethyl 2-bromo-4-methyl-3-oxopentanoate
→
CCOC(=O)c1sc(N)nc1C(C)C
product
Yield 40.6%
CCOC(=O)c1sc(N)nc1C(C)C
Ethyl 2-amino-4-isopropylthiazole-5-carboxylate
Yield 40.6%

Reactants

NC(N)=S
thiourea
CCOC(=O)C(Br)C(=O)C(C)C
Ethyl 2-bromo-4-methyl-3-oxopentanoate

Reagents

None

Solvents

CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureto reflux
  2. 2
    Temperaturethe reaction mixture refluxed further for 1 h
  3. 3
    Concentrationwas concentrated in vacuum

Procedure

A solution of thiourea (1.1 g) in ethanol (10 mL) was brought to reflux. Ethyl 2-bromo-4-methyl-3-oxopentanoate (3.0 g) was then added and the reaction mixture refluxed further for 1 h. The reaction was complete (by TLC) and was concentrated in vacuum. Flash chromatography (100% DCM→90:10 DCM:MeOH) afforded the product (1.1 g).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: USRE045323E1uspto-grants-2015_01