Ethylenediamine → N-methyl-N'-[2-(3-pyridazinylmethylamino)ethyl]thiourea
Reaction equation
ClCC1N=NC=CC=1.C(N)CN.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][NH:20][CH2:21][CH2:22][NH2:23])[N:14]=1.[CH3:24][N:25]=[C:26]=[S:27]>>[CH3:24][NH:25][C:26]([NH:23][CH2:22][CH2:21][NH:20][CH2:19][C:15]1[N:14]=[N:13][CH:18]=[CH:17][CH:16]=1)=[S:27]Participants
5
Procedure
Reacting 3-chloromethylpyridazine with ethylenediamine by the procedure of Example 34 and reacting the resulting N-(3-pyridazinylmethyl)ethylenediamine with methyl isothiocyanate by the procedure of Example 3(b), then chromatographing gives N-methyl-N'-[2-(3-pyridazinylmethylamino)ethyl]thiourea. This intermediate is reacted with lead cyanamide by the procedure of Example 3(b) to give N-cyano-N'-methyl-N"-[2-(3-pyridazinylmethylamino)ethyl]guanidine. Hydrolysis of this compound by the procedure of Example 3(e) gives N-methyl-N'-[2-(3-pyridazinylmethylamino)ethyl]guanidine dihydrochloride.
Sources & evidence
- ORD record
- ord-8912f82ae83b4b87b7d15e4d4eb787f2
- Source dataset
- uspto-grants-1977_05
- Patent number
- US04024271
Reaction notes
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