Ethylenediamine → N-(2-thiazolylmethyl)ethylenediamine

HRID 1577255Notes

Reaction equation

[CH2:1]([NH2:4])[CH2:2][NH2:3].Cl[CH2:6][C:7]1[S:8][CH:9]=[CH:10][N:11]=1>>[S:8]1[CH:9]=[CH:10][N:11]=[C:7]1[CH2:6][NH:3][CH2:2][CH2:1][NH2:4]

Participants

Reactant 2

HCID 3301Ethylenediamine

HCID 140908642-(Chloromethyl)-1,3-thiazole

Product 1

HCID 17944882N-(2-thiazolylmethyl)ethylenediamine

Procedure

Reacting ethylenediamine with 2-chloromethylthiazole by the procedure of Example 34 gives N-(2-thiazolylmethyl)ethylenediamine. Reacting this intermediate with S-methyl-N-nitroisothiourea by the procedure of Example 2(ii) gives N-nitro-N'-[2-(2-thiazolylmethylamino)ethyl]guanidine. Treatment with hydrobromic acid gives the hydrobromide salt.

Sources & evidence

ORD record: ord-661d7f20aa1d44ecab90fad524cb3340
Source dataset: uspto-grants-1981_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04287198

Reaction notes

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