Dimethylformamide → HCID 59769276, compound

HRID 2217963Notes

Reaction equation

HRID 2217963 reaction equation
P(Cl)(Cl)([Cl:3])=O.[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([F:14])[C:8]=1[CH:15]1[C:24](=O)[NH:23][C:22]2[CH:21]=[CH:20][N:19]=[N:18][C:17]=2C1=O.CN(C=O)C.[CH2:32]([Cl:34])Cl>ClCCCl>[Cl:3][C:24]1[C:15]([C:8]2[C:7]([F:6])=[CH:12][C:11]([F:13])=[CH:10][C:9]=2[F:14])=[C:32]([Cl:34])[C:17]2[N:18]=[N:19][CH:20]=[CH:21][C:22]=2[N:23]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 59769253HCID 59769253, compound

Product 1

HCID 59769276HCID 59769276, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Phosphorus oxychloride (0.048 ml) was added to the product from Step 3 (0.05 g) in 1,2-dichloroethane (2 ml) containing a catalytic amount of DMF. The suspension was stirred and refluxed for 1 hour and then stood for 18 hours, and then refluxed for a further hour and then allowed to cool. The excess phosphorus oxychloride was evaporated to give a brown oil, which was dissolved in DCM and washed with cold water. The organic layer was separated and dried over magnesium sulphate, filtered and evaporated to give a brown oil, which was purified by flash column chromatography on silica gel (40-60) eluting with diethyl ether to give 6,8-dichloro-7-(2,4,6-trifluorophenyl)-pyrido[3,2-c]pyridazine as a yellow oil (0.015 g).

Workup

  1. temperaturerefluxed for 1 hour
  2. temperaturerefluxed for a further hour
  3. temperatureto cool
  4. customThe excess phosphorus oxychloride was evaporated
  5. customto give a brown oil, which
  6. washwashed with cold water
  7. customThe organic layer was separated
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated
  11. customto give a brown oil, which
  12. customwas purified by flash column chromatography on silica gel (40-60)
  13. washeluting with diethyl ether

Sources & evidence

ORD record
ord-2f393218f4c741108b024bd8d93502bf
Source dataset
uspto-grants-2008_08
Patent number
US07410967B2

Reaction notes

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