5-Aminopentan-1-ol → N-cyano-N'-(5-hydroxypentyl)-N"-methylguanidine

HRID 2083093Notes

Reaction equation

HRID 2083093 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[C:8]([NH:10][C:11](=[N:14][CH3:15])SC)#[N:9]>N1C=CC=CC=1>[C:8]([NH:10][C:11]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7])=[N:14][CH3:15])#[N:9]

Participants

4

Reactant 2

HCID 756345-Aminopentan-1-olHCID 1111031-Cyano-2,3-dimethylisothiourea

Product 1

HCID 54552768N-cyano-N'-(5-hydroxypentyl)-N"-methylguanidineYield 44%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5-aminopentan-1-ol (20 g.) and N-cyano-N',S-dimethylisothiourea (25 g.) in pyridine (130 ml) was heated on a steam-bath for 14 hours, evaporated to dryness, and the residue recrystallised from chloroform/methanol to give N-cyano-N'-(5-hydroxypentyl)-N"-methylguanidine (15.7 g). A recrystallised sample had m.p. 116°-119°.

Workup

  1. temperaturewas heated on a steam-bath for 14 hours
  2. customevaporated to dryness
  3. customthe residue recrystallised from chloroform/methanol

Sources & evidence

ORD record
ord-0c29a52548724e7cb11a16f2ff51a744
Source dataset
uspto-grants-1978_04
Patent number
US04084001

Reaction notes

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