Benzoyl Peroxide → 2-Acetoxymethyl-6-bromomethyl-7-chloro-3,4-dihydroquinazolin-4-one
Reaction equation
[C:1]([O:4][CH2:5][C:6]1[NH:15][C:14](=[O:16])[C:13]2[C:8](=[CH:9][C:10]([Cl:18])=[C:11]([CH3:17])[CH:12]=2)[N:7]=1)(=[O:3])[CH3:2].[Br:19]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([O:4][CH2:5][C:6]1[NH:15][C:14](=[O:16])[C:13]2[C:8](=[CH:9][C:10]([Cl:18])=[C:11]([CH2:17][Br:19])[CH:12]=2)[N:7]=1)(=[O:3])[CH3:2]Participants
Procedure
To a suspension of 2-acetoxymethyl-7-chloro-6-methyl-3,4-dihydroquinazolin-4-one (2.00 g, 7.5 mmol) in anhydrous carbon tetrachloride (120 ml) was added N-bromosuccinimide (1.47 g, 8.3 mmol) followed by dibenzoyl peroxide (7.0 mg) under argon. The reaction mixture was placed in a preheated oil bath at 120° C. and stirred at this temperature for 3.5 hours while illuminating. The solvent was removed in vacuo and the residue was twice purified by column chromatography using 40% ethyl acetate in chloroform as eluant (1.02 g, 40%), mp 190-195° C., 1H-NMR (DMSO-d6) 2.14 (s, 3H, CH3CO), 4.91, 4.97 (2×s, 4H, 2-CH2 and 6-CH2), 7.78 (s, 1H, 8-H), 8.36 (s, 1H, 5-H), 12.61 (s, 1H, N3—H). This product was used in the next experiment without any further purification.
Workup
- customThe reaction mixture was placed in a preheated oil bath at 120° C.
- customwhile illuminating
- customThe solvent was removed in vacuo
- customthe residue was twice purified by column chromatography
- customThis product was used in the next experiment without any further purification
Sources & evidence
- ORD record
- ord-0f70542f86e346e4b9ccd8bdcace0f7f
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06699861B1
Reaction notes
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