4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole → HCID 13137359, compound

HRID 2166698Notes

Reaction equation

HRID 2166698 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].[N+](N[C:16]1[NH:21][C:20](=[O:22])[C:19]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][N:31]([CH3:33])[CH3:32])=[CH:26][CH:25]=2)=[CH:18][N:17]=1)([O-])=O>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:16]1[NH:21][C:20](=[O:22])[C:19]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][N:31]([CH3:32])[CH3:33])=[CH:26][CH:25]=2)=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 13137348HCID 13137348, compound

Product 1

HCID 13137359HCID 13137359, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(5-methyl-4-imidazolylmethylthio)ethylamine (1.37 g) and 2-nitroamino-5-(4-dimethylaminomethylbenzyl)-4-pyrimidone (2.27 g) in ethanol (12 ml) was heated under reflux for 24 hr. The ethanol was evaporated at reduced pressure giving 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(4-dimethylaminomethylbenzyl)-4-pyrimidone which was washed by mixing it with water, warming the mixture, allowing it to cool over about 16 hr. and decanting the water. The residue was reacted with ethanolic hydrochloric acid (7 ml) and ethanol removed at reduced pressure. The residue was recrystallised from methanol/ethanol to give the trihydrochloride (2.14 g) as a white solid m.p. 213.5°-216° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hr
  3. customThe ethanol was evaporated at reduced pressure

Sources & evidence

ORD record
ord-51c331a00a7146ed936d6cffd7f4de24
Source dataset
uspto-grants-1983_06
Patent number
US04388317

Reaction notes

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