Ethylenediamine → N-methyl-N'-[2-(3-isothiazolylmethylamino)ethyl]thiourea
Reaction equation
BrCC1C=[CH:6][S:5]N=1.C(N)[CH2:9][NH2:10].[S:12]1[CH:16]=[CH:15][C:14]([CH2:17][NH:18][CH2:19][CH2:20][NH2:21])=[N:13]1.[N-]=C=S>>[CH3:9][NH:10][C:6]([NH:21][CH2:20][CH2:19][NH:18][CH2:17][C:14]1[CH:15]=[CH:16][S:12][N:13]=1)=[S:5]Participants
5
Procedure
Reaction of 3-bromomethylisothiazole with ethylenediamine by the procedure of Example 34 and reaction of the resulting N-(3-isothiazolylmethyl)ethylenediamine with methyl (isothiocyanate by the procedure of Example 3(b) and then chromatographing gives N-methyl-N'-[2-(3-isothiazolylmethylamino)ethyl]thiourea. This intermediate is reacted with lead cyanamide by the procedure of Example 3(b) to give N-cyano-N'-[2-(3-isothiazolylmethylamino)ethyl]-N"-mathylguanidine. Hydrolysis of the last prepared compound by the procedure of Example 3(e) gives N-[2-(3-isothiazolylmethylamino)ethyl]-N'-methylguanidine dihydrochloride.
Sources & evidence
- ORD record
- ord-e5bd80efa05b43999478130e3448b4bf
- Source dataset
- uspto-grants-1977_09
- Patent number
- US04049672
Reaction notes
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