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

HRID 35650

Reaction equation

HRID 35650 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].[CH3:19][NH:20][C:21](=S)[NH:22][NH2:23]>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:21]([NH:20][CH3:19])=[N:22][N:23]=3)[N:13]=2)[CH:7]=1)[C:3](=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 2723853N-MethylhydrazinecarbothioamideHCID 15595702N-Methyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide

Product 1

HCID 15595689N-Methyl-N-[3-[3-(methylamino)-1,2,4-triazolo[4,3-b]pyridazin-6-yl]phenyl]acetamideYield 30.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6.0 g N-methyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide and 4.8 g 4-methylthiosemicarbazide in 200 ml ethanol was refluxed for 5 hours and treated in similar fashion in Example 67. Chromatography on silica gel with dichloromethane-methanol (96:4) and recrystalization from dichloromethane-hexane afforded 2.1 g yellow crystals, mp 213°-215° C.

Workup

  1. additiontreated in similar fashion in Example 67
  2. customChromatography on silica gel with dichloromethane-methanol (96:4) and recrystalization from dichloromethane-hexane

Sources & evidence

ORD record
ord-068f8c38ae0d447b911a6b90870572bf
Source dataset
uspto-grants-1988_08
Patent number
US04767765

Linked notes

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