4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole → 3-[2-(5-Methyl-4-imidazolylmethylthio)ethylamino]-6-(3-methoxybenzyl)-1,2,4-triazin-5-one

HRID 27216Notes

Reaction equation

HRID 27216 reaction equation
CS[C:3]1[NH:8][C:7](=[O:9])[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[N:5][N:4]=1.[CH3:19][C:20]1[NH:24][CH:23]=[N:22][C:21]=1[CH2:25][S:26][CH2:27][CH2:28][NH2:29]>>[CH3:19][C:20]1[NH:24][CH:23]=[N:22][C:21]=1[CH2:25][S:26][CH2:27][CH2:28][NH:29][C:3]1[NH:8][C:7](=[O:9])[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[N:5][N:4]=1

Participants

3

Reactant 2

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 1356242923-Methylthio-6-(3-methoxybenzyl)-1,2,4-triazin-5-one

Product 1

HCID 1357031873-[2-(5-Methyl-4-imidazolylmethylthio)ethylamino]-6-(3-methoxybenzyl)-1,2,4-triazin-5-oneYield 41.4%

Procedure

3-Methylthio-6-(3-methoxybenzyl)-1,2,4-triazin-5-one (1.07 g) and 2-(5-methyl-4-imidazolylmethylthio)ethylamine (0.77 g) were heated together on an oil bath (160°-70°) for 3/4 hour. The solidified mass was broken up under methanol (ea 15 ml) and boiled for 5 minutes. After cooling the white solid was filtered off and recrystallised from dimethylformamide to give the title compound as a colourless solid (0.65 g) m.p. 203°-4°.

Workup

  1. temperatureAfter cooling the white solid
  2. filtrationwas filtered off
  3. customrecrystallised from dimethylformamide

Sources & evidence

ORD record
ord-1dad164bd6f941439668105f13560607
Source dataset
uspto-grants-1980_09
Patent number
US04220767

Reaction notes

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