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

HRID 329115Notes

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 concenrating and separating by column chromatography, the title compound.

Workup

customto give
customseparating by column chromatography

Sources & evidence

ORD record: ord-2431cb88d58448ea9b04aa1790e12e6c
Source dataset: uspto-grants-1977_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04018931

Reaction notes

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