N-Nitro-S-methylisothiourea → HCID 178433317, compound

HRID 903687Notes

Reaction equation

HRID 903687 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].CS[C:14](=[NH:19])[NH:15][N+:16]([O-:18])=[O:17]>CO>[CH3:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:14]([NH:15][N+:16]([O-:18])=[O:17])=[NH:19]

Participants

4

Reactant 2

HCID 135927615N-Nitro-S-methylisothioureaHCID 178433288HCID 178433288, compound

Product 1

HCID 178433317HCID 178433317, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole (1.7 g.) and S-methyl-N-nitroisothiourea (1.45 g.) in methanol (35 ml.) was heated at 50°-60° for 2.5 hours and then set aside at room temperature for 48 hours. The crystalline product was filtered off and recrystallized from methanol to give N-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-N'-nitroguanidine, m.p. 184°-186°. (Found: C, 37.5; H, 5.7; N, 32.5; S, 12.5. C8H14N6O2S requires: C, 37.2; H, 5.5; N, 32.5; S, 12.4). (iii) Similarly reaction of N,S-dimethyl-N'-nitroisothiourea (1.6 g.) (m.p. 146°-147°, formed by the treatment of N,S-dimethylisothiouronium methosulphate with fuming nitric acid and concentrated sulphuric acid at -20°) with 4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole by the above procedure followed by chromatographic purification on a column of silica gel with acetone as eluant, gives N-methyl-N'-[2-((4 -methyl-5-imidazolyl)methylthio)ethyl]-N"-nitroguanidine (1.23 g.), m.p. 112°-114°. (Found: C, 39.5; H, 6.2; N, 30.6; S, 11.5 C9H16N6O2S requires: C, 39.7; H, 5.9; N, 30.9; S, 11.8.

Workup

  1. filtrationThe crystalline product was filtered off
  2. customrecrystallized from methanol

Sources & evidence

ORD record
ord-6e93720cec40420ab9b1b6a93488e134
Source dataset
uspto-grants-1980_10
Patent number
US04228291

Reaction notes

Loading…