Phosphorus oxychloride → HCID 15451777, compound
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
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
- stirringthe mixture was stirred
- temperatureunder reflux for 2 hours
- concentrationThe reaction mixture was concentrated under reduced pressure
- stirringthe solution was stirred into ice-water
- extractionThe organic phase was extracted in succession with water, saturated sodium hydrogencarbonate and sodium chloride solution
- customdried
- filtrationAfter filtering off with suction through neutral alumina, it
- concentrationwas concentrated
- stirringthe residue was stirred with ether and ether/pentane
- filtrationfiltered off with suction
- customdried
Sources & evidence
- ORD record
- ord-88b38edb5060458d8eaf40154537a649
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05571774
Reaction notes
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