Triethylamine → N-Methyl[5-phenyl-4-(3-pyridyl)-1,3-thiazol-2-yl]amine

HRID 1167653Notes

Reaction equation

HRID 1167653 reaction equation
[CH3:1][NH:2][C:3]([NH2:5])=[S:4].Br.Br[CH:8]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:9]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=O.C(N(CC)CC)C>C(#N)C>[CH3:1][NH:2][C:3]1[S:4][C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723704MethylthioureaHCID 134660052-Bromo-2-phenyl-1-(3-pyridyl)ethanone hydrobromide

Product 1

HCID 9838243N-Methyl[5-phenyl-4-(3-pyridyl)-1,3-thiazol-2-yl]amineYield 83.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-methylthiourea (484 mg) in acetonitrile (40 mL), was added 2-bromo-2-phenyl-1-(3-pyridyl)ethanone hydrobromide (2.0 g), and then triethylamine (0.8 mL) was added dropwise to the mixture with stirring. After addition, the resulting mixture was stirred at reflux for 3 h and the solvent was evaporated. An aqueous saturated solution of sodium hydrogen carbonate was added to the residue and extracted with ethyl acetate. The extracts were washed with water, dried and the solvent was evaporated. The crystalline residue was recrystallized from ethyl acetate-isopropyl ether to give the title compound (1.2 g, yield 80%).

Workup

  1. additionAfter addition
  2. stirringthe resulting mixture was stirred
  3. temperatureat reflux for 3 h
  4. customthe solvent was evaporated
  5. additionAn aqueous saturated solution of sodium hydrogen carbonate was added to the residue
  6. extractionextracted with ethyl acetate
  7. washThe extracts were washed with water
  8. customdried
  9. customthe solvent was evaporated
  10. customThe crystalline residue was recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-537c355ca2c14826998bbb4e6389b6ee
Source dataset
uspto-grants-2003_09
Patent number
US06620825B1

Reaction notes

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