Thiourea → Ethyl 2-amino-4-(propan-2-yl)-1,3-thiazole-5-carboxylate
Reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].Br[CH:6]([C:12](=O)[CH:13]([CH3:15])[CH3:14])[C:7]([O:9][CH2:10][CH3:11])=[O:8]>C(O)C>[NH2:1][C:2]1[S:3][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:12]([CH:13]([CH3:15])[CH3:14])[N:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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).
Workup
- temperatureto reflux
- temperaturethe reaction mixture refluxed further for 1 h
- concentrationwas concentrated in vacuum
Sources & evidence
- ORD record
- ord-757bce8d5c33420980255c8d8a6e7596
- Source dataset
- uspto-grants-2015_01
- Patent number
- USRE045323E1
Reaction notes
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