Sodium hydride → 2-Chloro-5-[[2-(nitromethylene)-3-thiazolidinyl]methyl]pyridine

HRID 376985

반응식

HRID 376985 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].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Cl)=[CH:17][N:16]=1>C(#N)C>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:9]2[CH2:8][CH2:7][S:6][C:5]2=[CH:4][N+:1]([O-:3])=[O:2])=[CH:17][N:16]=1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 38355832-Nitromethylene-thiazolidineHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 545653852-Chloro-5-[[2-(nitromethylene)-3-thiazolidinyl]methyl]pyridine수율 29.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

2-Nitromethylenethiazolidine (2.9 g) was dissolved in dry acetonitrile (30 ml), and 60% sodium hydride (0.9 g) was added at room temperature in a stream of nitrogen. Subsequently, the mixture was stirred at room temperature until the generation of hydrogen ceased. Then, a solution of 2-chloro-5-pyridylmethyl chloride (3.2 g) in dry acetonitrile (5 ml) was added at room temperature, and the mixture was stirred at room temperature for 1 day. Acetonitrile was then distilled off under reduced pressure, and dichloromethane was added to the residue. The mixture was then washed with water. Dichloromethane was distilled off from the dichloromethane layer. The remaining oil was purified by silica gel column chromatography to give the desired 3-(2-chloro-5-pyridylmethyl)-2-nitromethylenethiazolidine (1.6 g).

후처리

  1. distillationAcetonitrile was then distilled off under reduced pressure, and dichloromethane
  2. additionwas added to the residue
  3. washThe mixture was then washed with water
  4. distillationDichloromethane was distilled off from the dichloromethane layer
  5. customThe remaining oil was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-731ccd25c58c4a64afeb4f07a9f6e306
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06022967

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