Water → 6-(1-chloro-2-oxo-2-phenylethyl)-2-isopropyl-3(2H)-pyridazinone

HRID 915012Notes

Reaction equation

HRID 915012 reaction equation
[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([CH2:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5]1)([CH3:3])[CH3:2].S(Cl)([Cl:23])(=O)=O.O.CCOC(C)=O>C(Cl)Cl>[Cl:23][CH:11]([C:6]1[CH:7]=[CH:8][C:9](=[O:10])[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=1)[C:12](=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24648Sulfuryl chlorideHCID 693314642-isopropyl-6-(2-oxo-2-phenylethyl)-3(2H)-pyridazinone

Product 1

HCID 858295066-(1-chloro-2-oxo-2-phenylethyl)-2-isopropyl-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-isopropyl-6-(2-oxo-2-phenylethyl)-3(2H)-pyridazinone (100 g) and sulfurylchloride (32.9 ml) in CH2Cl2 (200 ml) was refluxed with stirring for 5 hours. Water and EtOAc were added to the reaction mixture. The organic layer was separated, and dried over MgSO4. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography eluted with a mixture of n-hexane and EtOAc. The fractions were concentrated in vacuo to obtain 6-(1-chloro-2-oxo-2-phenylethyl)-2-isopropyl-3(2H)-pyridazinone (100 g) as white powder.

Workup

  1. temperaturewas refluxed
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluted with a mixture of n-hexane and EtOAc
  7. concentrationThe fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-1148ceb74662448d84e3c15ad4dca89d
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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