Phosphorus pentachloride → HCID 57672582, compound

HRID 1671669Notes

Reaction equation

HRID 1671669 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.O1CCOCC1.[CH:13]1([NH:16][C:17](=O)[C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([CH3:27])[CH:19]=2)[CH2:15][CH2:14]1.[N-:29]=[N+:30]=[N-:31].[Na+]>O.C1(C)C=CC=CC=1>[CH:13]1([N:16]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([CH3:27])[CH:19]=3)=[N:31][N:30]=[N:29]2)[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 24819Phosphorus pentachlorideHCID 312751,4-DioxaneHCID 33557Sodium AzideHCID 4620448HCID 4620448, compound

Product 1

HCID 57672582HCID 57672582, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

6.3 g (30 mmol) of phosphorus pentachloride was added to a mixture of 40 ml of toluene and 4 ml of dioxane containing 4.7 g (21 mmol) of N-cyclopropyl-3-methyl-4-nitrobenzamide and the mixture was heated to reflux for three hours. The reaction mixture was concentrated under reduced pressure, then dissolved in 30 ml of DMF and slowly added dropwise to a DMF solution containing 2.8 g (43 mmol) of sodium azide. The reaction mixture was stirred for five hours, then poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was filtered and washed with ether to obtain 3.7 g of the desired compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for three hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutiondissolved in 30 ml of DMF
  5. additionslowly added dropwise to a DMF solution
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. filtrationThe residue was filtered
  10. washwashed with ether

Sources & evidence

ORD record
ord-683b3115c8a34b9e8830f03101c9d50c
Source dataset
uspto-grants-2011_08
Patent number
US07994339B2

Reaction notes

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