Water → HCID 18412022, compound

HRID 992263Notes

Reaction equation

HRID 992263 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][N:9]=[C:10]([C:14](=O)[CH3:15])[C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[CH2:24][C:25](Cl)=[O:26].O>O1CCCC1>[C:11]([C:10]1[C:14]([CH3:15])=[C:24]([C:20]2[S:19][CH:23]=[CH:22][CH:21]=2)[C:25](=[O:26])[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[N:9]=1)(=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1623622-Thiopheneacetyl chlorideHCID 178468332HCID 178468332, compound

Product 1

HCID 18412022HCID 18412022, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Pentan-2,3,4-trione 3-(3-chlorophenylhydrazone) (2.39 g) was added to a suspension of 66% sodium hydride (0.77 g) in anhydrous tetrahydrofuran (40 ml) under ice cooling, followed by stirring at room temperature for 30 minutes. Then, a solution of 2-thiopheneacetyl chloride (1.77 g) in anhydrous tetrahydrofuran (10 ml) was added dropwise under ice cooling, followed by stirring at room temperature for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. After washing with water and a brine, the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by evaporation, the resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4), and the resulting crude crystals were washed with hexane to obtain 6-acetyl-2-(3-chlorophenyl)-5-methyl-4-(2-thienyl)-3(2H)-pyridazinone (2.19 g) (Compound No. 1-97).

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. washAfter washing with water
  4. dry with materiala brine, the organic layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by evaporation
  6. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4)
  7. washthe resulting crude crystals were washed with hexane

Sources & evidence

ORD record
ord-e1bc2b7cee7a46858755f1e62a75dd9f
Source dataset
uspto-grants-2002_10
Patent number
US06469003B1

Reaction notes

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