Hydrochloric Acid → 6-benzoyl-3,4-dihydro-2(1H)-quinazolinone

HRID 2247886Notes

Reaction equation

HRID 2247886 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][NH:16][C:15]1=[O:24].Cl>CN(C)C=O>[C:5]([C:20]1[CH:19]=[C:18]2[C:23](=[CH:22][CH:21]=1)[NH:14][C:15](=[O:24])[NH:16][CH2:17]2)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 123607561,2,3,4-Tetrahydroquinazolin-2-one

Product 1

HCID 198160376-benzoyl-3,4-dihydro-2(1H)-quinazolinoneYield 76.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a vigorously stirred amount of 45 parts of aluminum chloride were added dropwise 7.05 parts of N,N-dimethylformamide. After stirring for 5 min. at 70° C., there were added 5 parts of benzoyl chloride and, dropwise, 4.7 parts of 3,4-dihydro-2(1H)-quinazolinone. Stirring was continued for 2 hours at 70° C. The reaction mixture was poured into ice-water and there were added 63.5 parts of HCl. The precipitate was filtered off and recrystallized from 2-methoxyethanol, yielding 6.5 parts (76.4%) of 6-benzoyl-3,4-dihydro-2(1H)-quinazolinone; mp. 264.8° C. (interm. 1).

Workup

  1. stirringStirring
  2. waitwas continued for 2 hours at 70° C
  3. filtrationThe precipitate was filtered off
  4. customrecrystallized from 2-methoxyethanol

Sources & evidence

ORD record
ord-38053b881e014e169f8a5f7fcffe0981
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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