Sulfuric Acid → 3-[7-Methyl-2-oxo-1-(propan-2-yl)-1,2-dihydroquinazolin-4-yl]phenyl acetate

Reaction equation

[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:14])[CH:12]=2)[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)=[N:6][C:5]1=[O:22])([CH3:3])[CH3:2].[C:23](OC(=O)C)(=[O:25])[CH3:24].S(=O)(=O)(O)O>>[C:23]([O:21][C:17]1[CH:16]=[C:15]([C:7]2[C:8]3[C:13](=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=3)[N:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:22])[N:6]=2)[CH:20]=[CH:19][CH:18]=1)(=[O:25])[CH3:24]

Participants

Reactant 3

HCID 1118Sulfuric Acid

HCID 7918Acetic Anhydride

HCID 632573-Hydroxyproquazone

Product 1

HCID 203719573-[7-Methyl-2-oxo-1-(propan-2-yl)-1,2-dihydroquinazolin-4-yl]phenyl acetate

Procedure

To 5.0 g of refined 1-isopropyl-4-(3-hydroxyphenyl)-7-methyl-2(1H)-quinazolinone in a vessel, is added 100 ml. of acetic anhydride and 0.5 ml of concentrated sulfuric acid. The resulting mixture is allowed to stand for 16 hours. The reaction mixture is then poured over salted ice in a vessel. After the ice has melted, the resulting liquid is extracted twice with 300 ml portions of benzene: n-butanol (4:1) and the combined extracts washed with distilled water until free of acid, and then evaporated to obtain a residue. The residue is crystallized from methanol to obtain the title product, m.p. 148°-150°.