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

HRID 1167653노트

반응식

HRID 1167653 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-537c355ca2c14826998bbb4e6389b6ee
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06620825B1

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