Ethylenediamine → N-Methyl-N'-[2-(2-thiazolylmethylamino)ethyl]urea

HRID 26884Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH:7][CH2:8][CH2:9][NH2:10].C(N)CN.ClCC1SC=CN=1.[CH3:22][N:23]=[C:24]=[O:25]>>[CH3:22][NH:23][C:24]([NH:10][CH2:9][CH2:8][NH:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][N:3]=1)=[O:25]

Participants

Reactant 4

HCID 3301Ethylenediamine

HCID 12228Methyl Isocyanate

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

HCID 17944882N-(2-thiazolylmethyl)ethylenediamine

Product 1

HCID 20557949N-Methyl-N'-[2-(2-thiazolylmethylamino)ethyl]urea

Procedure

N-(2-Thiazolylmethyl)ethylenediamine, prepared by reacting ethylenediamine with 2-chloromethylthiazole by the procedure of Example 40, is reacted with methyl isocyanate by the procedure of Example 24 to give, after concentrating and separating by column chromatography, the title compound.

Workup

customto give
concentrationafter concentrating
customseparating by column chromatography

Sources & evidence

ORD record: ord-b7dab71b839d4a05b74897068e5ade89
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04151288

Reaction notes

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