Dimethylformamide → HCID 57743124, compound

HRID 910136Notes

Reaction equation

HRID 910136 reaction equation
[H-].[Na+].CN(C=O)C.[NH:8]1[CH:12]=[N:11][CH:10]=[N:9]1.Cl[C:14]1[C:19]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[C:18]([CH3:27])[N:17]=[N:16][C:15]=1[CH3:28]>C(OCC)(=O)C>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([C:19]2[C:14]([N:8]3[CH:12]=[N:11][CH:10]=[N:9]3)=[C:15]([CH3:28])[N:16]=[N:17][C:18]=2[CH3:27])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 57743122HCID 57743122, compound

Product 1

HCID 57743124HCID 57743124, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

87 mg of sodium hydride (55% oil dispersion) was added to 5 ml of DMF. To this was added 0.14 g of 1,2,4-triazole, and the mixture was stirred for 0.5 hours at room temperature. To the resultant mixture was added 0.25 g of 4-chloro-5-(4-chlorophenyl)-3,6-dimethylpyridazine, and the mixture was stirred for 3 hours on an oil bath of 80° C. To the reaction mixture was added ethyl acetate, and the mixture was washed with brine four times. The organic layer was dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure. 0.39 g of the resultant residue was subjected to silica gel column chromatography, to obtain 0.20 g of 5-(4-chlorophenyl)-3,6-dimethyl-4-(1,2,4-triazol-1-yl)pyridazine (hereinafter, described as compound (7) of the present invention.).

Workup

  1. stirringthe mixture was stirred for 3 hours on an oil bath of 80° C
  2. washthe mixture was washed with brine four times
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4aca1b65cddf4d8b995b3bb185efcf71
Source dataset
uspto-grants-2011_09
Patent number
US08022073B2

Reaction notes

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