Ethylenediamine → 6-[3-bromo-4-(1,3-diazacyclopenten-2-ylamino)-phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone

HRID 1247887Notes

Reaction equation

HRID 1247887 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][C:3]=1[Br:16].CS[N:19]=[C:20]=O.[CH2:22](N)[CH2:23][NH2:24]>>[Br:16][C:3]1[CH:4]=[C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)[CH:6]=[CH:7][C:2]=1[NH:1][C:20]1[NH:19][CH2:22][CH2:23][N:24]=1

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 202792156-(4-Amino-3-bromophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-oneHCID 21933440Methylthioisocyanate

Product 1

HCID 132173476-[3-bromo-4-(1,3-diazacyclopenten-2-ylamino)-phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone

Procedure

Using 6-(4-amino-3-bromophenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone and methylthioisocyanate, the reaction was carried out in the same manner as described in Example 1(b) to the corresponding methylisothiuronium salt which was then reacted with ethylenediamine in the same manner as described in Example 1(c) to afford the above-identified compound. M.P. 265°-267° C. (with decomp.).

Workup

  1. customto afford the above-identified compound

Sources & evidence

ORD record
ord-7edb9ac9cca4413199e59b4400518b73
Source dataset
uspto-grants-1985_06
Patent number
US04521415

Reaction notes

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