4-Ethyl-3-thiosemicarbazide → N-Methyl-N-[3-[3-(ethylamino)-1,2,4-triazolo[4,3-b]pyridazin-6-yl]phenyl]acetamide

HRID 329645Notes

Reaction equation

HRID 329645 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[N:13]=[N:14][C:15](Cl)=[CH:16][CH:17]=2)[CH:7]=1)[C:3](=[O:5])[CH3:4].[CH2:19]([NH:21][C:22](=S)[NH:23][NH2:24])[CH3:20]>C(O)C>[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]3[N:14]([C:22]([NH:21][CH2:19][CH3:20])=[N:23][N:24]=3)[N:13]=2)[CH:7]=1)[C:3](=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 15517804-Ethyl-3-thiosemicarbazideHCID 15595702N-Methyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide

Product 1

HCID 15595690N-Methyl-N-[3-[3-(ethylamino)-1,2,4-triazolo[4,3-b]pyridazin-6-yl]phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6.0 g -N-methyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide and 5.5 g 4-ethyl-3-thiosemicarbazide in 200 ml ethanol was refluxed for 18 hours and treated in similar fashion to Example 67. Chromatography on silica gel and recrystalization from dichloromethanehexane afforded 1.2 g yellow crystals, mp 225°-227° C.

Workup

  1. additiontreated in similar fashion to Example 67
  2. customChromatography on silica gel and recrystalization from dichloromethanehexane

Sources & evidence

ORD record
ord-c8544cc5e6cc44f4bb7ec0c2ae612bd1
Source dataset
uspto-grants-1990_01
Patent number
US04892873

Reaction notes

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