Sodium hydride → 1-(2-Chloro-5-pyridylmethyl)-3,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine

HRID 635173Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][N:6]([CH3:8])[CH2:5][NH:4][C:3]1=[N:9][N+:10]([O-:12])=[O:11].[H-].[Na+].[H][H].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24]Cl)=[CH:20][N:19]=1>CN(C=O)C>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:4]2[CH2:5][N:6]([CH3:8])[CH2:7][N:2]([CH3:1])[C:3]2=[N:9][N+:10]([O-:12])=[O:11])=[CH:20][N:19]=1

Participants

Conditions

Temperature: 50 °C

Procedure

1 g of 1,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine was dissolved in 20 ml of dried DMF. To the solution, 0.27 g of 60% sodium hydride was added with cooling. The mixture was stirred for 1 hour at room temperature until evolution of hydrogen was ceased and then the mixture was heated with stirring further for 1 hour at 50° C. To the mixture, a solution of 0.9 g of 2-chloro-5-pyridylmethylchloride in 8 ml of dried DMF was added dropwise at 40-50° C. After this addition, the reaction mixture was heated with stirring it for two hours at 70-80° C. The mixture was poured into ice-water and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate, and dichloromethane was distilled off. The residue was purified by a column chromatography to obtain 1.3 g of the title compound. This compound is No.5 in Table 1. m.p.: 116-117° C.

Workup

temperaturewith cooling
temperaturethe mixture was heated
additionAfter this addition
temperaturethe reaction mixture was heated
stirringwith stirring it for two hours at 70-80° C
extractionextracted with dichloromethane
dry with materialThe extract was dried over anhydrous magnesium sulfate, and dichloromethane
distillationwas distilled off
customThe residue was purified by a column chromatography

Sources & evidence

ORD record: ord-74b0577c3044412799547f7d72b53aaf
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06187773B1

Reaction notes

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