Carbon Disulfide → HCID 18918808, compound

HRID 1291399Notes

Reaction equation

HRID 1291399 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][N:5]([CH3:8])[C:4](=[O:9])[C:3]=1Cl.[H-].[Na+].[C:13](=[S:15])=[S:14].[F:16][C:17]1[CH:32]=[CH:31][C:20]([C:21]([C:23]2[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=2)=[O:22])=[CH:19][CH:18]=1>CN(C=O)C>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([C:23]2[CH:30]=[CH:29][C:26]([CH2:27][S:14][C:13]3[S:15][C:3]4[C:4](=[O:9])[N:5]([CH3:8])[N:6]=[CH:7][C:2]=4[N:1]=3)=[CH:25][CH:24]=2)=[O:22])=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 594330MethyldesphenylchloridazonHCID 47290134-(4-Fluorobenzoyl)benzyl bromide

Product 1

HCID 18918808HCID 18918808, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (10 ml) was dissolved 5-amino-4-chloro-2-methyl-3(2H)-pyridazinone (638 mg) followed by addition of 60% sodium hydride (384 mg), and the mixture was stirred at room temperature for 10 minutes. Then, carbon disulfide (365 mg) was added and the mixture was further stirred at 80° C. for 1 hour. Thereafter, 4-(4-fluorobenzoyl)benzyl bromide (1.4 g) was added and the mixture was stirred at room temperature for 1 hour. This reaction mixture was extracted with ethyl acetate-THF and the organic layer was washed serially with water and saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel chromatography (hexane: ethyl acetate =1:1) to provide 1.2 g of white powder.

Workup

  1. stirringthe mixture was further stirred at 80° C. for 1 hour
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. extractionThis reaction mixture was extracted with ethyl acetate-THF
  4. washthe organic layer was washed serially with water and saturated aqueous NaCl solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (hexane: ethyl acetate =1:1)

Sources & evidence

ORD record
ord-272a232e11fd462ebb03db7980be83c6
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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