2-Pentanone → N-(2-phenylethyl)-4-propyl-1,3-thiazole-2-amine

HRID 732167

Reaction equation

HRID 732167 reaction equation
[CH3:1][C:2](=O)[CH2:3][CH2:4][CH3:5].BrBr.C([O-])(=O)C.[Na+].[C:14]1([CH2:20][CH2:21][NH:22][C:23]([NH2:25])=[S:24])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])O.[Na+]>CO>[C:14]1([CH2:20][CH2:21][NH:22][C:23]2[S:24][CH:1]=[C:2]([CH2:3][CH2:4][CH3:5])[N:25]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 78952-PentanoneHCID 24408Bromine2×HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 735845(2-Phenylethyl)thiourea

Product 1

HCID 23143297N-(2-phenylethyl)-4-propyl-1,3-thiazole-2-amineYield 23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-pentanone (1.72 g) in methanol (10 mL) was added bromine (3.20 g) at −30° C. The mixture was allowed to warm to room temperature and stirred until the red color of bromine disappeared. To the obtained colorless solution were added sodium acetate (3.20 g) and N-(2-phenylethyl)thiourea (2.70 g) and the mixture was stirred with heating under reflux for 4 hr. A saturated aqueous sodium hydrogencarbonate solution (10 mL) was added to the reaction mixture and the mixture was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio) to give the title compound (850 mg, yield 23%) as pale-yellow crystals.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 4 hr
  3. concentrationthe mixture was concentrated
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio)

Sources & evidence

ORD record
ord-8a7dc02c80cc4c78acd0931c4bf26a5d
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Linked notes

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