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

HRID 231175Notes

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).

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-77a45a7be4434a7b858cb16dcff6b94f
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04845106

Reaction notes

Loading…