3-(Chloromethyl)pyridine → 3-(3-Pyridylmethyl)2-nitromethylenethiazolidine

HRID 231172

반응식

HRID 231172 반응식
[N+:1]([CH:4]=[C:5]1[NH:9][CH2:8][CH2:7][S:6]1)([O-:3])=[O:2].[H-].[Na+].[H][H].[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20]Cl)[CH:15]=1>C(#N)C>[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:9]2[CH2:8][CH2:7][S:6][C:5]2=[CH:4][N+:1]([O-:3])=[O:2])[CH:15]=1

참가 물질

6

반응물 4

HCID 183583-(Chloromethyl)pyridineHCID 24758Sodium hydrideHCID 38355832-Nitromethylene-thiazolidineHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 542512073-(3-Pyridylmethyl)2-nitromethylenethiazolidine수율 10.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

2-Nitromethylenethiazolidine (2.9 g) was suspended in dry acetonitrile (30 ml), and 60% sodium hydride (0.9 g) was added under a nitrogen stream. Then, the mixture was stirred at room temperature until the generation of hydrogen ceased. A solution of 3-picolyl chloride (3.2 g) in dry acetonitrile (5 ml) was added, and the mixture was stirred at room temperature for 3 hours. Acetonitrile was distilled off under reduced pressure. Dichloromethane was added to the residue, and the mixture was washed with water. Dichloromethane was then distilled off from the dichloromethane layer. The remaining oily product was purified by column chromatography to give the desired 3-(3-pyridylmethyl)2-nitromethylenethiazolidine (0.5 g).

후처리

  1. distillationAcetonitrile was distilled off under reduced pressure
  2. additionDichloromethane was added to the residue
  3. washthe mixture was washed with water
  4. distillationDichloromethane was then distilled off from the dichloromethane layer
  5. customThe remaining oily product was purified by column chromatography

출처 및 근거

ORD 기록
ord-2c9768b86e0a44aeabf6cfeff8924499
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04845106

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