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

HRID 461773Notes

Reaction equation

HRID 461773 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

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 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°.

Workup

  1. additionThe reaction mixture is then poured over salted ice in a vessel
  2. extractionthe resulting liquid is extracted twice with 300 ml portions of benzene: n-butanol (4:1)
  3. washthe combined extracts washed with distilled water until free of acid
  4. customevaporated
  5. customto obtain a residue
  6. customThe residue is crystallized from methanol

Sources & evidence

ORD record
ord-e4d7ef810ce249d19b99fb1428f2910c
Source dataset
uspto-grants-1977_12
Patent number
US04064246

Reaction notes

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