Sodium Carbonate → 6-[3-(2-Chloromethyl-3-methylpyridin-4-ylsulfanyl)propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazine

HRID 1637615노트

반응식

HRID 1637615 반응식
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[C:7]([CH2:29]O)=[N:8][CH:9]=[CH:10][C:11]=1[S:12][CH2:13][CH2:14][CH2:15][S:16][C:17]1[CH:18]=[CH:19][C:20]2[N:21]([C:23]([N+:26]([O-:28])=[O:27])=[CH:24][N:25]=2)[N:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Cl:3][CH2:29][C:7]1[C:6]([CH3:5])=[C:11]([S:12][CH2:13][CH2:14][CH2:15][S:16][C:17]2[CH:18]=[CH:19][C:20]3[N:21]([C:23]([N+:26]([O-:28])=[O:27])=[CH:24][N:25]=3)[N:22]=2)[CH:10]=[CH:9][N:8]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 9908482{3-Methyl-4-[3-(3-nitroimidazo[1,2-b]pyridazin-6-ylsulfanyl)propylsulfanyl]pyridin-2-yl}methanol

생성물 1

HCID 187993836-[3-(2-Chloromethyl-3-methylpyridin-4-ylsulfanyl)propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazine수율 97.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

A solution of 3.6 ml (49.8 mmol) of thionyl chloride in 30 ml of dichloromethane is added dropwise at room temperature to a solution of 15.0 g (38.3 mmol) of {3-methyl-4-[3-(3-nitroimidazo[1,2-b]pyridazin-6-yl-sulfanyl)propylsulfanyl]pyridin-2-yl}methanol in 400 ml of anhydrous dichloromethane and the mixture is then stirred for a further 18 h. It is then cooled to 0° C. and aqueous sodium carbonate solution (100 ml) is cautiously added dropwise. The dichloromethane is distilled off. The suspension is then treated with 400 ml of water and stirred at 0° C. for 30 min. The precipitate is filtered off, washed with water, dried at 40° C. in vacuo and then suspended in 300 ml of acetone. After filtration and drying, 15.3 g (97%) of the title compound are isolated as a beige powder. M.p.: 155-156° C.

후처리

  1. distillationThe dichloromethane is distilled off
  2. additionThe suspension is then treated with 400 ml of water
  3. stirringstirred at 0° C. for 30 min
  4. filtrationThe precipitate is filtered off
  5. washwashed with water
  6. customdried at 40° C. in vacuo
  7. filtrationAfter filtration
  8. customdrying

출처 및 근거

ORD 기록
ord-922c000721ad49ada57f78799c0371e7
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06043242

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