N-(2-chloro-5-pyridylmethyl)trimethylenediamine → 1-(2-Chloro-5-pyridylmethyl)-2-(nitroimino)tetrahydropyrimidine

HRID 2211034Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH2:11][CH2:12][NH2:13])=[CH:4][N:3]=1.[N+:14]([NH:17][C:18](N)=N)([O-:16])=[O:15]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:10][CH2:11][CH2:12][NH:13][C:18]2=[N:17][N+:14]([O-:16])=[O:15])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution composed of N-(2-chloro-5-pyridylmethyl)trimethylenediamine (10 g), nitroguanidine (5.7 g) and water (80 ml) was heated at 80° C. for 3 hours. The reaction mixture was cooled to room temperature, and extracted twice with 50 ml of dichloromethane. Dichloromethane was distilled off from the extracts, and the tarry residue was purified by silica gel column chromatography to give almost colorless 1-(2-chloro-5-pyridylmethyl)-2-(nitroimino)tetrahydropyrimidine (6.1 g). mp. 113°-117° C.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted twice with 50 ml of dichloromethane
distillationDichloromethane was distilled off from the extracts
customthe tarry residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-c2e68b26343f4feeb58718b03b9fc92e
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05461167

Reaction notes

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