Dichloromethane → 2-Benzyl-5-iodopyridazin-3(2H)-one

HRID 2046384Notes

Reaction equation

HRID 2046384 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12](Cl)=[C:11](Cl)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl.S([O-])([O-])(=O)=S.[Na+].[Na+].[IH:27]>>[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]=[C:11]([I:27])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 24477Sodium ThiosulfateHCID 24841Hydrogen iodideHCID 7224382-Benzyl-4,5-dichloro-2,3-dihydropyridazin-3-one

Product 1

HCID 469421452-Benzyl-5-iodopyridazin-3(2H)-one

Conditions

Temperature
115 °C

Procedure

2-Benzyl-4,5-dichloropyridazin-3(2H)-one (32.3 g, 127 mmol) was dissolved in hydriodic acid (223 mL) and the mixture was refluxed at 115° C. overnight. The mixture was poured into dichloromethane and 30% sodium thiosulphate (250 mL), and extracted with dichloromethane (3×250 mL). The combined organics were washed with 30% sodium thiosulphate several times (total 1 L), dried (sodium sulfate), and concentrated. Dichloromethane was added to the residue and the precipitate was collected by filtration to afford the title compound. 1H NMR (500 MHz, CD3SOCD3) δ 8.17 (s, 1H); 7.61 (s, 1H); 7.23-7.33 (m, 5H); 5.17 (s, 2H). LRMS (APCI) calc'd for (C11H10IN2O) [M+H]+, 313.0. found 313.0.

Workup

  1. extractionextracted with dichloromethane (3×250 mL)
  2. washThe combined organics were washed with 30% sodium thiosulphate several times (total 1 L)
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. additionDichloromethane was added to the residue
  6. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-9a89c77f7abb4b7581a64c66c8a2de0d
Source dataset
uspto-grants-2013_11
Patent number
US08592425B2

Reaction notes

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