Thiourea → Ethyl 2-amino-4-(propan-2-yl)-1,3-thiazole-5-carboxylate

HRID 241682Notes

Reaction equation

HRID 241682 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]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 13015595Ethyl 2-bromo-4-methyl-3-oxopentanoate

Product 1

HCID 824436Ethyl 2-amino-4-(propan-2-yl)-1,3-thiazole-5-carboxylateYield 40.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. temperatureto reflux
  2. temperaturethe reaction mixture refluxed further for 1 h
  3. concentrationwas concentrated in vacuum

Sources & evidence

ORD record
ord-225c56d04bc94e20bd404bb7d5563c22
Source dataset
uspto-grants-2014_02
Patent number
US08653075B2

Reaction notes

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