Diethylamine → N,N-Diethyl-N′-nitroguanidine

HRID 1781585Notes

Reaction equation

HRID 1781585 reaction equation
CS[C:3](=[NH:8])[NH:4][N+:5]([O-:7])=[O:6].[CH2:9]([NH:11][CH2:12][CH3:13])[CH3:10]>C(#N)C>[CH2:9]([N:11]([CH2:12][CH3:13])[C:3]([NH:4][N+:5]([O-:7])=[O:6])=[NH:8])[CH3:10]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 135927615N-Nitro-S-methylisothiourea

Product 1

HCID 135794776N,N-Diethyl-N′-nitroguanidineYield 53.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 1.35 g of S-methyl-N-nitroisothiourea and 5 ml of acetonitrile was added 0.88 g of diethylamine, followed by stirring for 6 hours in an oil bath of 60° C. The reaction mixture was concentrated and the residue was purified by a column chromatography [developing solvent: dichloromethanemethanol (20:1)] to afford 0.85 g of N,N-diethyl-N'-nitroguanidine as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by a column chromatography [developing solvent: dichloromethanemethanol (20:1)]

Sources & evidence

ORD record
ord-0ae21637521349e3a5ce4e7dee9dae97
Source dataset
uspto-grants-1997_05
Patent number
US05633375

Reaction notes

Loading…