Phosphorus oxychloride → HCID 15451777, compound

HRID 619702Notes

Reaction equation

HRID 619702 reaction equation
[C:1]([N:5]1[C:14](=[O:15])[C:13]2[C:8](=[N+:9]([O-])[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=2)[C:6]1=[O:7])([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:22])=O>>[C:1]([N:5]1[C:14](=[O:15])[C:13]2[C:8](=[N:9][C:10]([Cl:22])=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=2)[C:6]1=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 15451776HCID 15451776, compound

Product 1

HCID 15451777HCID 15451777, compound

Procedure

100 ml of phosphoryl chloride were treated with 7.5 g (0.028 mol) of N-tert-butyl-5-nitropyridine-2,3-dicarboximide-1-oxide at 60° C. and in portions in the course of 2 minutes with stirring and the mixture was stirred under reflux for 2 hours. The reaction mixture was concentrated under reduced pressure, the residue was taken up in methylene chloride and the solution was stirred into ice-water. The organic phase was extracted in succession with water, saturated sodium hydrogencarbonate and sodium chloride solution and dried. After filtering off with suction through neutral alumina, it was concentrated and the residue was stirred with ether and ether/pentane, filtered off with suction and dried. 4.49 g (56% of theory) of the title compound of m.p. 100-104° C. were obtained (active compound Example 1.019).

Workup

  1. stirringthe mixture was stirred
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. stirringthe solution was stirred into ice-water
  5. extractionThe organic phase was extracted in succession with water, saturated sodium hydrogencarbonate and sodium chloride solution
  6. customdried
  7. filtrationAfter filtering off with suction through neutral alumina, it
  8. concentrationwas concentrated
  9. stirringthe residue was stirred with ether and ether/pentane
  10. filtrationfiltered off with suction
  11. customdried

Sources & evidence

ORD record
ord-802fbf4db2bb455d97104b30e2718e70
Source dataset
uspto-grants-1999_09
Patent number
US05959116

Reaction notes

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