N-Benzylacetamide → 3-benzyl-7-chloro-2-methylquinazolin-4(3H)-one

HRID 547452

Reaction equation

HRID 547452 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:12]([NH:19][C:20](=O)[CH3:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>P(Cl)(Cl)(Cl)=O>[CH2:12]([N:19]1[C:4](=[O:6])[C:3]2[C:2](=[CH:10][C:9]([Cl:11])=[CH:8][CH:7]=2)[N:1]=[C:20]1[CH3:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 11500N-BenzylacetamideHCID 666462-Amino-4-chlorobenzoic acid

Product 1

HCID 583781963-benzyl-7-chloro-2-methylquinazolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

2-Amino-4-chlorobenzoic acid (250 mg, 1 eq.) and N-benzylacetamide (261 mg, 1.2 eq.) were dissolved in phosphorus oxychloride (2 ml). The reaction was placed in the microwave for 10 minutes at 150° C. The reaction was quenched by pouring the mixture into ice. The crude product was extracted into ethyl acetate. The ethyl acetate layer was washed with water, 10% aqueous sodium hydroxide, dried with magnesium sulfate, filtered, and concentrated to yield 3-benzyl-7-chloro-2-methylquinazolin-4 (3H)-one as an orange solid.

Workup

  1. customThe reaction was quenched
  2. additionby pouring the mixture into ice
  3. extractionThe crude product was extracted into ethyl acetate
  4. washThe ethyl acetate layer was washed with water, 10% aqueous sodium hydroxide
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6d9d58d3257b4282bb0988a4d0392c84
Source dataset
uspto-grants-2011_05
Patent number
US07939539B2

Linked notes

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