Phosphorus pentachloride → HCID 59443043, compound

HRID 1959145Notes

Reaction equation

HRID 1959145 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[CH3:7][C:8]1([CH3:22])[NH:13][C:12](=O)[C:11]2[CH:15]=[CH:16][C:17]([N+:19]([O-:21])=[O:20])=[CH:18][C:10]=2[O:9]1>P(Cl)(Cl)(Cl)=O>[Cl:2][C:12]1[C:11]2[CH:15]=[CH:16][C:17]([N+:19]([O-:21])=[O:20])=[CH:18][C:10]=2[O:9][C:8]([CH3:22])([CH3:7])[N:13]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 529881742,2-Dimethyl-7-nitro-2,3-dihydro-4H-1,3-benzoxazin-4-one

Product 1

HCID 59443043HCID 59443043, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

Phosphorus pentachloride (5.5 g) was added to a solution of 2,2-dimethyl-7-nitro-3,4-dihydro-2H-1,3-benzoxazine-4-one (4 g) in phosphoryl chloride (15 mL) at 0° C., and the mixture was stirred at room temperature for one hour. The mixture was heated to 60° C. and stirred at the same temperature overnight. After cooling to 0° C., the reaction mixture was poured into ice water (300 mL). After stirring for 30 minutes, the mixture was extracted with ethyl acetate (100 mL×2). The combined organic layer was washed with brine (100 mL×2), dried over sodium sulfate and concentrated in vacuo to give the titled compound (2.34 g) as a brown oil, which was used in the next step without further purification.

Workup

  1. temperatureThe mixture was heated to 60° C.
  2. stirringstirred at the same temperature overnight
  3. temperatureAfter cooling to 0° C.
  4. stirringAfter stirring for 30 minutes
  5. extractionthe mixture was extracted with ethyl acetate (100 mL×2)
  6. washThe combined organic layer was washed with brine (100 mL×2)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f5e4f335f4c1472b95583d0a81828385
Source dataset
uspto-grants-2013_04
Patent number
US08410166B2

Reaction notes

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