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

HRID 1441461Notes

Reaction equation

[NH4+:1].C([O-])(=O)C.ClC(Cl)(Cl)[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:13][C:12]=1[C:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=1)=[O:9]>CS(C)=O>[Cl:34][C:30]1[CH:29]=[C:28]([C:27]2[C:12]3[C:11](=[CH:16][CH:15]=[C:14]([C:17](=[O:26])[C:18]4[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=4)[CH:13]=3)[NH:10][C:8](=[O:9])[N:1]=2)[CH:33]=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Acetic acid, ammonium salt (0.107 mol) was added at room temperature to a mixture of intermediate 12 (0.0536 mol) in DMSO (250 ml). The mixture was stirred at 60° C. for 4 hours then brought to room temperature, poured out into ice water and stirred. The precipitate was filtered, washed with water and taken up in warm CH3CN. The precipitate was filtered, washed with diethyl ether and dried under a vacuo, yielding 16.2 g (77%) of intermediate 13. The mother layer was evaporated. The residue was purified by column chromatography over silica gel (15-40 μm) (eluent: DCM/MeOH/NH4OH; 95/5/0.1). The pure fractions were collected and the solvent was evaporated. The residue (1.2 g, 6%) was crystallized from 2-propanone. The precipitate was filtered off and dried, yielding 0.9 g (4%) of 4—(3-chlorophenyl)-6-(4-methoxybenzoyl)-2(1H)quinazolinone (intermediate 13), mp. 248° C.

Workup

customthen brought to room temperature
stirringstirred
filtrationThe precipitate was filtered
washwashed with water
filtrationThe precipitate was filtered
washwashed with diethyl ether
customdried under a vacuo

Sources & evidence

ORD record: ord-458b67b9b60a4232ab6bc1342d0e4a4e
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655654B2

Reaction notes

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