Benzoyl chloride → 5-[3-(Benzoyloxy)propylthio]imidazo[1,2-a]pyridine

HRID 1081733노트

반응식

HRID 1081733 반응식
[OH:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[N:11]2[CH:12]=[CH:13][N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[C:22]([O:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[N:11]2[CH:12]=[CH:13][N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 233628905-[3-(Hydroxy)propylthio]imidazo[1,2-a]pyridine

생성물 1

HCID 233629675-[3-(Benzoyloxy)propylthio]imidazo[1,2-a]pyridine수율 88.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 5-[3-(hydroxy)propylthio]imidazo[1,2-a]pyridine (1.00 g, 4.80 mmoles) and triethylamine (0.80 ml, 5.74 mmoles) in methylene chloride (25 ml) was added benzoyl chloride (1.10 ml, 11.6 moles) with stirring at room temperature and the mixture was further stirred at room temperature for 30 minutes. The reaction mixture was washed with an aqueous 1N sodium hydroxide solution and dried. After the solvent was distilled off, the residue was purified by column chromatography [eluent:hexane/acetone (1:1)] to obtain 1.32 g of the desired product (88.1%, white solid).

후처리

  1. stirringthe mixture was further stirred at room temperature for 30 minutes
  2. washThe reaction mixture was washed with an aqueous 1N sodium hydroxide solution
  3. customdried
  4. distillationAfter the solvent was distilled off
  5. customthe residue was purified by column chromatography [eluent:hexane/acetone (1:1)]

출처 및 근거

ORD 기록
ord-17bc351322f544d48809a5a3bbe6481a
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05587383

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