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Water → 1-(2-Chloro-5-pyridylmethyl)-5-methyl-2-nitroiminohexahydro-1,3,5-triazine

HRID 862390
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HRID 862390 반응식
[CH3:1][N:2]1[CH2:7][NH:6][C:5](=[N:8][N+:9]([O-:11])=[O:10])[NH:4][CH2:3]1.[H-].[Na+].[Cl:14][C:15]1N=[CH:19][C:18]([CH2:21]Cl)=[CH:17][N:16]=1.O.[CH3:24]N(C)C=O.CN(C=O)C>CN(C=O)C>[Cl:14][C:15]1[CH:24]=[CH:19][C:18]([CH2:21][N:6]2[CH2:7][N:2]([CH3:1])[CH2:3][NH:4][C:5]2=[N:8][N+:9]([O-:11])=[O:10])=[CH:17][N:16]=1
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참가 물질

7

반응물 5

HCID 962WaterHCID 24758Sodium hydrideHCID 17824068DMF dimethylformamideHCID 220528832-Chloro-5-(chloromethyl)pyrimidineHCID 1354673605-Methyl-2-nitroimino-hexahydro-1,3,5-triazine

생성물 1

HCID 1364010691-(2-Chloro-5-pyridylmethyl)-5-methyl-2-nitroiminohexahydro-1,3,5-triazine

시약·촉매·용매

1
HCID 6228Dimethylformamide용매

실험 절차

5-Methyl-2-nitroimino-hexahydro-1,3,5-triazine (3.0 g) was dissolved in dimethylformamide/DMF (20 ml), followed by portionwise addition of sodium hydride (950 mg: oil free) thereto at a temperature in the range of from 0° to 5° C. After one hour stirring at 0° to 5° C. a solution of 2-chloro-5-chloromethyl-pyrimidine (3.1 g) in 20 ml of DMF was added dropwise to the solution, the temperature was kept constant, followed by a five hour stirring. The reaction mixture thus obtained was poured into iced water, subjected to extraction with methylene chloride a few times and then the extract was dried with anhydrous magnesium sulfate which was removed from the solvent. The thus obtained residue was purified by silica gel column chromatography (eluant: ethanol: chloroform=1: 20), to obtain the desired 1-(2-chloro-5-pyridylmethyl)-5-methyl-2-nitroimino-hexahydro-1,3,5-triazine (3.7 g) having a melting point in the range of from 160° to 161° C.

후처리

  1. customof from 0° to 5° C
  2. additionwas added dropwise to the solution
  3. customThe reaction mixture thus obtained
  4. extractionsubjected to extraction with methylene chloride a few times
  5. dry with materialthe extract was dried with anhydrous magnesium sulfate which
  6. customwas removed from the solvent
  7. customThe thus obtained residue was purified by silica gel column chromatography (eluant: ethanol: chloroform=1: 20)

출처 및 근거

ORD 기록
ord-4226ff06c93043f4bde3603d05b18598
출처 데이터셋
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05719146

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