Hydrochloric Acid → 1-Prpopanesulfonamide, N,N-dimethyl-3-((1,2,4)triazolo(1,5-b)pyridazin-6-yloxy)-

HRID 274283

Reaction equation

HRID 274283 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:12])[S:5]([CH2:8][CH2:9][CH2:10][OH:11])(=[O:7])=[O:6].Cl[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([N:20]=[CH:21][N:22]=2)[N:19]=1.Cl>CN(C)C=O>[CH3:3][N:4]([CH3:12])[S:5]([CH2:8][CH2:9][CH2:10][O:11][C:14]1[CH:15]=[CH:16][C:17]2[N:18]([N:20]=[CH:21][N:22]=2)[N:19]=1)(=[O:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 112406116-Chloro-(1,2,4)triazolo(1,5-b)pyridazineHCID 152348883-hydroxy-N,N-dimethylpropane-1-sulfonamide

Product 1

HCID 30738021-Prpopanesulfonamide, N,N-dimethyl-3-((1,2,4)triazolo(1,5-b)pyridazin-6-yloxy)-Yield 73.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 10 ml of dimethylformamide was suspended 0.252 g of 60% sodium hydride in oil followed by addition of 1.0 g of N,N-dimethyl-3-hydroxypropane-1-sulfonamide and the mixture was stirred under reduced pressure at room temperature for 30 minutes. Then, 0.928 g of 6-chloro[1,2,4]triazolo[1,5-b]pyridazine was added and the mixture was further stirred at room temperature for 1.5 hours. Following addition of 30 ml of ice water, the reaction mixture was adjusted to pH 4.0 with 1N-hydrochloric acid and the resulting crystals were collected by filtration and recrystallized from hot methanol to provide 1.255 g of the title compound. m.p. 151°-153° C.

Workup

  1. stirringthe mixture was further stirred at room temperature for 1.5 hours
  2. filtrationthe resulting crystals were collected by filtration
  3. customrecrystallized from hot methanol

Sources & evidence

ORD record
ord-e7189cad2c3c4360b95b56d9cd977bbf
Source dataset
uspto-grants-1995_02
Patent number
US05389633

Linked notes

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