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

HRID 1167653ノート

反応式

HRID 1167653 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-537c355ca2c14826998bbb4e6389b6ee
出典データセット
uspto-grants-2003_09
特許番号
US06620825B1

反応ノート

読み込み中…