Ethylenediamine → N-methyl-N'-[2-(3-isothiazolylmethylamino)ethyl]thiourea
Reaction equation
BrCC1C=CSN=1.C(N)CN.[S:12]1[CH:16]=[CH:15][C:14]([CH2:17][NH:18][CH2:19][CH2:20][NH2:21])=[N:13]1.[CH3:22][N:23]=[C:24]=[S:25]>>[CH3:22][NH:23][C:24]([NH:21][CH2:20][CH2:19][NH:18][CH2:17][C:14]1[CH:15]=[CH:16][S:12][N:13]=1)=[S:25]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"-methylguanidine. 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-e9ddf51d161046ffabceb93d19aaab7f
- Source dataset
- uspto-grants-1977_05
- Patent number
- US04024271
Reaction notes
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