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 376989
Notes
Print preview

Reaction equation

HRID 376989 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. temperatureThe reaction mixture was 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-8b6024714b7741538a8e67b766e9d919
Source dataset
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06022967

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes