Ethylenediamine → N-Methyl-N'-[2-(3-isothiazolylmethylamino)ethyl]urea

HRID 26888Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][NH:7][CH2:8][CH2:9][NH2:10])=[N:2]1.C(N)CN.BrCC1C=CSN=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:3]1[CH:4]=[CH:5][S:1][N:2]=1)=[O:25]

Participants

Reactant 4

HCID 3301Ethylenediamine

HCID 12228Methyl Isocyanate

HCID 130375983-(bromomethyl)Isothiazole

HCID 20557777N-(3-isothiazolylmethyl)ethylenediamine

Product 1

HCID 20557581N-Methyl-N'-[2-(3-isothiazolylmethylamino)ethyl]urea

Procedure

N-(3-Isothiazolylmethyl)ethylenediamine, prepared by reacting ethylenediamine with 3-bromomethylisothiazole by the procedure of Example 40(a), 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-fe698912d47b499d8d612bdfb135dcf8
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04151288

Reaction notes

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