Phosphorus oxychloride → 4-Chloro-6-nitroquinazoline

HRID 240567

Reaction equation

HRID 240567 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][N:8]=[C:7]2O)([O-:3])=[O:2].C(N(C(C)C)C(C)C)C.P(Cl)(Cl)([Cl:26])=O>ClC(Cl)C>[Cl:26][C:7]1[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 178526470HCID 178526470, compound

Product 1

HCID 113562574-Chloro-6-nitroquinazoline

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-nitroquinazolin-4-ol (4.40 g, 23.01 mmol) and N-ethyl-N-isopropylpropan-2-amine (11.89 g, 92.04 mmol) in dichloroethane (50 mL) was added phosphoryl trichloride (7.06 g, 46.02 mmol). After heating to 80° C. for 16 hours, the mixture was concentrated under reduced pressure. The residue was concentrated again with toluene (2×100 mL) to provide the product.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. concentrationThe residue was concentrated again with toluene (2×100 mL)
  3. customto provide the product

Sources & evidence

ORD record
ord-d1eed894f6634d29a3b589e41d38d8f6
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Linked notes

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