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

HRID 2163911Notes

Reaction equation

HRID 2163911 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

5

Reactant 4

HCID 3301EthylenediamineHCID 12228Methyl IsocyanateHCID 130375983-(bromomethyl)IsothiazoleHCID 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

  1. customto give
  2. concentrationafter concentrating
  3. customseparating by column chromatography

Sources & evidence

ORD record
ord-9e614501dc794010bbf70a31479901b7
Source dataset
uspto-grants-1979_01
Patent number
US04137234

Reaction notes

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