Water → 4-(3-chlorophenyl)-6-(4-fluorobenzoyl)-2(1H)-quinazolinone

HRID 1788043Notes

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

Participants

Conditions

Temperature: 60 °C

Procedure

Acetic acid, ammonium salt (0.135 mol) was added at room temperature to a mixture of intermediate 4 (0.0675 mol) in DMSO (300 ml). The mixture was stirred at 60° C. for 4 hours, then brought to room temperature and poured out into water. The precipitate was filtered, washed with water, taken up in warm CH3CN, filtered, washed again with CH3CN, then with diethyl ether and dried under a vacuo, yielding 18.5 g (72%) of intermediate 5. The mother layer 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 was crystallized from 2-propanone/diethyl ether. The precipitate was filtered off and dried, yielding 1.8 g (7%) of 4-(3-chlorophenyl)-6-(4-fluorobenzoyl)-2(1H)-quinazolinone (intermediate 5), mp. 226° C.

Workup

custombrought to room temperature
filtrationThe precipitate was filtered
washwashed with water
filtrationfiltered
washwashed again with CH3CN
dry with materialwith diethyl ether and dried under a vacuo

Sources & evidence

ORD record: ord-4053017f320e42749ffe11e63cb6b74b
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511138B2

Reaction notes

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