Thiourea → 4-(Propan-2-yl)-1,3-thiazol-2-amine

HRID 1009051Notes

Reaction equation

HRID 1009051 reaction equation
Br[CH2:2][C:3](=O)[CH:4]([CH3:6])[CH3:5].[NH2:8][C:9]([NH2:11])=[S:10]>C(O)C>[CH:4]([C:3]1[N:8]=[C:9]([NH2:11])[S:10][CH:2]=1)([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 108990371-Bromo-3-methylbutan-2-one

Product 1

HCID 70640774-(Propan-2-yl)-1,3-thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
57.5 °C

Procedure

To a solution of the above prepared 1-bromo-3-methyl-butan-2-one (3.58 g, 21.6 mmol) in 40 mL of ethanol was added thiourea (1.64 g, 1.00 eq.) and the mixture vigorously stirred at 55-60° C. for 3 h. Pouring onto crashed ice/Na2CO3, twofold extraction with ethyl acetate, washing with water and brine, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/ethyl acetate=6/4), left 2.996 g of the title product as colorless oil.

Workup

  1. additionPouring
  2. extractionice/Na2CO3, twofold extraction with ethyl acetate
  3. washwashing with water and brine
  4. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  5. waitleft 2.996 g of the title product as colorless oil

Sources & evidence

ORD record
ord-1a6f94e4ef754a35bdd61b8ffcb015dc
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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