Ammonium Acetate → 4-(3-chlorophenyl)-6-(4-methylbenzoyl)-2(1H)-quinazolinone

HRID 1788060Notes

Reaction equation

HRID 1788060 reaction equation
ClC(Cl)(Cl)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:8][C:7]=1[C:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)=[O:4].[NH4+:32].C([O-])(=O)C>CS(C)=O>[Cl:28][C:24]1[CH:23]=[C:22]([C:21]2[C:7]3[C:6](=[CH:11][CH:10]=[C:9]([C:12](=[O:20])[C:13]4[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=4)[CH:8]=3)[NH:5][C:3](=[O:4])[N:32]=2)[CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 686890442,2,2-trichloro-N-[2-(3-chlorobenzoyl)-4-(4-methylbenzoyl)phenyl]-acetamide

Product 1

HCID 686874324-(3-chlorophenyl)-6-(4-methylbenzoyl)-2(1H)-quinazolinoneYield 63.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of intermediate 21 (0.0085 mol) and acetic acid, ammonium salt (0.0169 mol) in DMSO (42 ml) was stirred at 60° C. for 4 hours then cooled and poured out into ice water. The precipitate was filtered, washed with water, taken up in warm CH3CN, filtered off and dried under a vacuo, yielding 2.02 g (63%) of 4-(3-chlorophenyl)-6-(4-methylbenzoyl)-2(1H)quinazolinone (intermediate 22), mp. >260° C.

Workup

  1. temperaturethen cooled
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. filtrationfiltered off
  5. customdried under a vacuo

Sources & evidence

ORD record
ord-ef68f45e67c84ed5b740f889c172e6d1
Source dataset
uspto-grants-2009_03
Patent number
US07511138B2

Reaction notes

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