Dimethylformamide → HCID 86658690, compound

HRID 42703Notes

Reaction equation

HRID 42703 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:4]=[N:3]1.O=P(Cl)(Cl)Cl.CN([CH:23]=[O:24])C>>[CH3:1][N:2]1[C:7](=[O:8])[C:6]([CH:23]=[O:24])=[C:5]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:4]=[N:3]1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 13103626HCID 13103626, compound

Product 1

HCID 86658690HCID 86658690, compound

Procedure

A solution of 2-methyl-5-(piperidin-1-yl)pyridazin-3(2H)-one [F. Farina, M. V. Martin and A. Tito, An. Quim., 77, 188-195 (1981)] (1.35 g, 7 mmol) in dry DMF (23.3 ml) was cooled to 5° C., then a solution of POCl3 (1.44 ml, 15.4 mmol) in dry DMF (3.5 ml) was added dropwise. The cooling bath was removed and the mixture was stirred at room temperature for 30 min. Then, the temperature was raised to 70° C. and stirring was continued for 75 min. After cooling, the volatile components were removed under reduced pressure and the residue was treated with crushed ice (15 g). The mixture was adjusted to pH 7-8 with aqueous NaOH. Then it was extracted with dichloromethane (4×40 ml) and the combined extracts were washed with water, dried (Na2SO4) and evaporated. Residual volatile material was removed at 10−2 mbar to leave an oily residue which slowly solidified on storage in a refrigerator.

Workup

  1. customThe cooling bath was removed
  2. temperatureThen, the temperature was raised to 70° C.
  3. stirringstirring
  4. waitwas continued for 75 min
  5. temperatureAfter cooling
  6. customthe volatile components were removed under reduced pressure
  7. additionthe residue was treated with crushed ice (15 g)
  8. extractionThen it was extracted with dichloromethane (4×40 ml)
  9. washthe combined extracts were washed with water
  10. dry with materialdried (Na2SO4)
  11. customevaporated
  12. customResidual volatile material was removed at 10−2 mbar
  13. customto leave an oily residue which

Sources & evidence

ORD record
ord-f9f8906397c24f32a7af4da36eeb348c
Source dataset
uspto-grants-2013_09
Patent number
US08536210B2

Reaction notes

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