Phosphorus pentachloride → 4-Chloro-8-nitroquinazoline

HRID 1469724

Reaction equation

HRID 1469724 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][NH:10][C:9]2=O)([O-:3])=[O:2].P(Cl)(Cl)(Cl)(Cl)[Cl:16]>O=P(Cl)(Cl)Cl>[Cl:16][C:9]1[C:8]2[C:13](=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][CH:7]=2)[N:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 1354087998-Nitroquinazolin-4-ol

Product 1

HCID 114584714-Chloro-8-nitroquinazolineYield 91.2%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A suspension of 8-nitroquinazolin-4(3H)-one (1.0 g, 5.23 mmol) and PCl5 (1.3 g, 6.24 mmol) in POCl3 (5 mL) was heated at reflux for 4 h. Then the reaction mixture was concentrated and the concentrate was diluted with Et2O. The precipitated solid was filtered and dried to afford 1.0 g of the title product. 1H NMR (300 MHz, DMSO d6): δ 9.25 (s, 1H), 8.71 (d, J=7.8 Hz, 1H), 8.59 (d, J=7.8 Hz, 1H), 8.07-8.02 (t, J=7.8 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. concentrationThen the reaction mixture was concentrated
  4. additionthe concentrate was diluted with Et2O
  5. filtrationThe precipitated solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-1f813e5c99c843f6a3592068cf5bb7ca
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Linked notes

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