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

HRID 1087097Notes

Reaction equation

HRID 1087097 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 1.35g of S-methyl-N-nitroisothiourea and 5ml of acetonitrile was added 0.88g 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 0.85g 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-f3a14ab79f8f41a584d7f90d0538ed6e
Source dataset
uspto-grants-1991_07
Patent number
US05034404

Reaction notes

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