Dimethylformamide → HCID 86658691, compound

HRID 42709Notes

Reaction equation

HRID 42709 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:13](=[O:14])[CH:12]=[C:11]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.O=P(Cl)(Cl)Cl.CN([CH:31]=[O:32])C>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:13](=[O:14])[C:12]([CH:31]=[O:32])=[C:11]([N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)[CH:10]=[N:9]2)=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 67446904HCID 67446904, compound

Product 1

HCID 86658691HCID 86658691, compound

Procedure

A solution of 2-(4-methoxybenzyl)-5-(morpholin-4-yl)pyridazin-3(2H)-one (6.22 g, 20.60 mmol) in dry DMF (60 ml) was cooled to 5° C., then a solution of POCl3 (4.21 ml, 45.1 mmol) in dry DMF (12 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 80 min. After cooling, the volatile components were removed under reduced pressure and the residue was treated with crushed ice (70 g). The mixture was adjusted to pH 7-8 with aqueous NaOH. Then it was extracted with ethyl acetate (2×60 ml) and the combined extracts were washed with water, dried (Na2SO4) and evaporated. The crude product was purified by crystallization from ethanol (95%).

Workup

  1. customThe cooling bath was removed
  2. temperatureThen, the temperature was raised to 70° C.
  3. stirringstirring
  4. waitwas continued for 80 min
  5. temperatureAfter cooling
  6. customthe volatile components were removed under reduced pressure
  7. additionthe residue was treated with crushed ice (70 g)
  8. extractionThen it was extracted with ethyl acetate (2×60 ml)
  9. washthe combined extracts were washed with water
  10. dry with materialdried (Na2SO4)
  11. customevaporated
  12. customThe crude product was purified by crystallization from ethanol (95%)

Sources & evidence

ORD record
ord-311dc6283dc14a00a911b9b5e9990a04
Source dataset
uspto-grants-2013_09
Patent number
US08536210B2

Reaction notes

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