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

HRID 35654

Reaction equation

HRID 35654 reaction equation
[CH3:1][N:2]([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:3](=[O:6])[CH2:4][CH3:5].[CH2:20]([NH:22][C:23](=S)[NH:24][NH2:25])[CH3:21]>>[CH3:1][N:2]([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:3](=[O:6])[CH2:4][CH3:5]

Participants

3

Reactant 2

HCID 15517804-Ethyl-3-thiosemicarbazideHCID 14280298N-methyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]propanamide

Product 1

HCID 15595695N-Methyl-N-[3-[3-(ethylamino)-1,2,4-triazolo[4,3-b]-pyridazin-6-yl]phenyl]propanamideYield 20.4%

Procedure

A solution of 5.0 g N-methyl-N-[3-(6-chloro-3-pyridazinyl)phenyl]propanamide and 4.3 g 4-ethyl-3-thiosemicarbazide was refluxed for 18 hours. The mixture was then treated and the product chromatographed as described in Example 70. Recrystalization of the product from dichloromethane-hexane afforded 1.2 g of yellow crystals, mp 198°-199° C.

Workup

  1. additionThe mixture was then treated
  2. customthe product chromatographed
  3. customRecrystalization of the product from dichloromethane-hexane

Sources & evidence

ORD record
ord-a731356be077480dbef05d8dbdd41a7c
Source dataset
uspto-grants-1988_08
Patent number
US04767765

Linked notes

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