Phosphorus pentachloride → HCID 59710096, compound

HRID 1864516Notes

Reaction equation

HRID 1864516 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][N:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][C:16]([N+:22]([O-:24])=[O:23])=[CH:17][CH:18]=2)[NH:13][C:12]1=O.P(Cl)(Cl)(Cl)(Cl)[Cl:27]>O=P(Cl)(Cl)Cl>[Cl:27][C:12]1[N:11]([CH2:10][CH2:9][C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[C:20](=[O:21])[C:19]2[C:14](=[CH:15][C:16]([N+:22]([O-:24])=[O:23])=[CH:17][CH:18]=2)[N:13]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 22174927HCID 22174927, compound

Product 1

HCID 59710096HCID 59710096, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

3-[2-(2,4-Dichlorophenyl)ethyl]-7-nitro-2,4(1H, 3H)-quinazolinedione (2.0 g, 5.26 mmol) and PCl5 (1.2 g, 5.79 mmol) were added to a flask containing POCl3 (20 mL) and the resulting solution was refluxed with stirring for 6 hours. The reaction was allowed to cool to RT and stirred overnight at this temp. The POCl3 was removed under reduced pressure and CH2Cl2 was added to the residue. The unreacted starting material was removed via vacuum filtration and the product was purified by silica gel flash chromatography (100% CH2Cl2 eluent) to give the product (0.96 g, 46% yield) as a white solid. 1H NMR (DMSO-D6) 400 MHz δ ppm 8.35-8.25 (m, 3H), 7.58 (d, J=2.2 Hz, 1H), 7.41-7.34 (m, 2H), 4.41 (t, J=7.5 Hz, 2H), 3.15 (t, J=7.5 Hz, 2H) ppm.

Workup

  1. temperaturethe resulting solution was refluxed
  2. stirringstirred overnight at this temp
  3. customThe POCl3 was removed under reduced pressure and CH2Cl2
  4. additionwas added to the residue
  5. customwas removed via vacuum filtration
  6. customthe product was purified by silica gel flash chromatography (100% CH2Cl2 eluent)

Sources & evidence

ORD record
ord-23fd3165136040979ec367e9b8ce4240
Source dataset
uspto-grants-2009_12
Patent number
US07625909B2

Reaction notes

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