Chloroacetaldehyde → HCID 18412006, compound

HRID 992267Notes

Reaction equation

HRID 992267 reaction equation
[C:1]([C:4]1[C:5]([CH3:21])=[C:6]([C:18]([NH2:20])=[S:19])[C:7](=[O:17])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[N:9]=1)(=[O:3])[CH3:2].Cl[CH2:23][CH:24]=O>C(O)C>[C:1]([C:4]1[C:5]([CH3:21])=[C:6]([C:18]2[S:19][CH:23]=[CH:24][N:20]=2)[C:7](=[O:17])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[N:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 18412000HCID 18412000, compound

Product 1

HCID 18412006HCID 18412006, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension (5 ml) of 6-acetyl-4-(aminothioxomethyl)-2-(3-chlorophenyl)-5-methyl-3(2H)-pyridazinone (200 mg) in ethanol (5 ml) was added a 50% aqueous solution of chloroacetoaldehyde, followed by heating under reflux for 10 hours. After cooling on standing, the reaction mixture was extracted with ethyl acetate. After washing with a saturated sodium hydrogen carbonate aqueous solution 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=1:2), and the resulting crude crystals was washed with hexane to obtain 6-acetyl-2-(3-chlorophenyl)-5-methyl-4-(1,3-thiazol-2-yl)-3(2H)-pyridazinone (90 mg) (Compound No. 1-155).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 10 hours
  3. temperatureAfter cooling
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washAfter washing with a saturated sodium hydrogen carbonate aqueous solution
  6. dry with materiala brine, the organic layer was dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by evaporation
  8. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2)
  9. washthe resulting crude crystals was washed with hexane

Sources & evidence

ORD record
ord-85cbe61f3d6d47908c6335706c1689fa
Source dataset
uspto-grants-2002_10
Patent number
US06469003B1

Reaction notes

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