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

HRID 1079424
Notes
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Reaction equation

HRID 1079424 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-8b06d0a349494c3baa22420aa926b699
Source dataset
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05580889

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes