HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 359507
Notes
Print preview

Reaction equation

HRID 359507 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 10703172N-(2-chloro-5-pyridylmethyl)trimethylenediamineHCID 86287517Nitroguanidine

Product 1

HCID 1363427891-(2-Chloro-5-pyridylmethyl)-2-(nitroimino)tetrahydropyrimidineYield 45.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. temperaturewas cooled to room temperature
  2. extractionextracted twice with 50 ml of dichloromethane
  3. distillationDichloromethane was distilled off from the extracts
  4. customthe tarry residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e60042c8a2864ecb9eb77f0402f10c37
Source dataset
uspto-grants-1991_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05001138

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes