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

HRID 1906827Notes

Reaction equation

HRID 1906827 reaction equation
[CH2:1]([N:3]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[N:14]=[N:15][C:16](Cl)=[CH:17][CH:18]=2)[CH:8]=1)[C:4](=[O:6])[CH3:5])[CH3:2].[CH2:20]([NH:22][C:23](=S)[NH:24][NH2:25])[CH3:21]>C(O)C>[CH2:1]([N:3]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]3[N:15]([C:23]([NH:22][CH2:20][CH3:21])=[N:24][N:25]=3)[N:14]=2)[CH:8]=1)[C:4](=[O:6])[CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 15517804-Ethyl-3-thiosemicarbazideHCID 14280297N-Ethyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide

Product 1

HCID 15595692N-Ethyl-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 7.0 g N-ethyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]acetamide and 6.0 g 4-ethyl-3-thiosemicarbazide in 200 ml ethanol was refluxed for 18 hours. The mixture was then worked up and the product chromatographed as described in Example 70. Recrystallization of the product from dichloromethane-hexane afforded 2.1 g yellow flakes, mp 171°-172° C.

Workup

  1. customthe product chromatographed
  2. customRecrystallization of the product from dichloromethane-hexane
  3. customafforded 2.1 g yellow flakes, mp 171°-172° C.

Sources & evidence

ORD record
ord-630dfa27424f47b0bda856e167b44e40
Source dataset
uspto-grants-1987_03
Patent number
US04654343

Reaction notes

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