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

HRID 1660252Notes

Reaction equation

HRID 1660252 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-825b1dfcb2ed45f29083132830b3db95
Source dataset
uspto-grants-1981_12
Patent number
US04307101

Reaction notes

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