Bromopinacolone → 4-tert-Butyl-1,3-thiazol-2-amine

HRID 421155Notes

Reaction equation

HRID 421155 reaction equation
Br[CH2:2][C:3](=O)[C:4]([CH3:7])([CH3:6])[CH3:5].[NH2:9][C:10]([NH2:12])=[S:11].C(=O)([O-])O.[Na+]>C(O)C>[NH2:12][C:10]1[S:11][CH:2]=[C:3]([C:4]([CH3:7])([CH3:6])[CH3:5])[N:9]=1

Participants

5

Reactant 3

HCID 21642BromopinacoloneHCID 516892Sodium BicarbonateHCID 2723790Thiourea

Product 1

HCID 27342024-tert-Butyl-1,3-thiazol-2-amineYield 90.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-bromo-3,3-dimethyl-2-butanone (5.03 g, 28.1 mmol), thiourea (2.35 g, 30.9 mmol) and ethanol (30 mL) was refluxed for 1.5 hours. After cooling, the reaction mixture was poured into saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (hexane:ethyl acetate=2:1 →1:1) to give the title compound (3.99 g, 90.9%) as a yellowish white powder.

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washAfter the organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe residue obtained by evaporation under reduced pressure
  7. customwas purified by chromatography on silica gel (hexane:ethyl acetate=2:1 →1:1)

Sources & evidence

ORD record
ord-ddca7d118f664733b2790399f17feb58
Source dataset
uspto-grants-2012_01
Patent number
US08097759B2

Reaction notes

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