4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole → CIMETIDINE,3-NITRO-4,5-DIHYDROPYRROL-YL ANALOG

HRID 1995589Notes

Reaction equation

HRID 1995589 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].CS[C:14]1[NH:15][CH2:16][CH2:17][C:18]=1[N+:19]([O-:21])=[O:20]>C(O)C>[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:14]1[NH:15][CH2:16][CH2:17][C:18]=1[N+:19]([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 13208971HCID 13208971, compound

Product 1

HCID 12831749CIMETIDINE,3-NITRO-4,5-DIHYDROPYRROL-YL ANALOGYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(5-methyl-4-imidazolylmethylthio)ethylamine (1.3 g, 0.0076 mol) and 2-methylthio-3-nitro-4,5-dihydropyrrole (1.2 g, 0.0075 mol) in ethanol (50 ml) was refluxed for 11/2 hours. The mixture was cooled, and the solid was filtered off and recrystallised from methanol/water to give 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-3-nitro-4,5-dihydropyrrole (1.4 g, 66%) m.p. 207.5°-208°. Found: C, 46.65; H, 6.15; N, 24.6; S, 11.5; C11H17N5O2S requires: C, 46.6; H, 6.05; N, 24.7; S, 11.3%.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe solid was filtered off
  3. customrecrystallised from methanol/water

Sources & evidence

ORD record
ord-120daec3370b4143b07c9d3bbd876915
Source dataset
uspto-grants-1983_09
Patent number
US04405624

Reaction notes

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