Ethanol → N-(2-phenylethyl)-4-(pyridin-2-yl)-1,3-thiazol-2-amine

HRID 732171

Reaction equation

HRID 732171 reaction equation
Br.Br[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=O.[C:12]1([CH2:18][CH2:19][NH:20][C:21]([NH2:23])=[S:22])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(=O)C.[Na+].C(O)C>O>[C:12]1([CH2:18][CH2:19][NH:20][C:21]2[S:22][CH:3]=[C:4]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=3)[N:23]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 517045Sodium AcetateHCID 735845(2-Phenylethyl)thioureaHCID 27762312-Bromo-1-(2-pyridinyl)-1-ethanone hydrobromide

Product 1

HCID 973106N-(2-phenylethyl)-4-(pyridin-2-yl)-1,3-thiazol-2-amineYield 67.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-bromo-1-pyridin-2-ylethanone hydrobromide (4.00 g), N-(2-phenylethyl)thiourea (3.60 g), sodium acetate (1.60 g) and ethanol (30 mL) was stirred with heating under reflux for 1 hr. After cooling, the reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and 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 (2.71 g, yield 48%) as a yellow oil.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 1 hr
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio)

Sources & evidence

ORD record
ord-0ab8515fa9534e92a621e505e97bfcb0
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Linked notes

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