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

HRID 1834762Notes

Reaction equation

HRID 1834762 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].S(=O)(=O)(O)O.[C:28](OC(=O)C)(=[O:30])[CH3:29]>>[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]([O:21][C:28](=[O:30])[CH3:29])[CH:16]=2)=[N:6][C:5]1=[O:22])([CH3:3])[CH3:2]

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-3a350b7954194e5a8904abda44d6a736
Source dataset
uspto-grants-1978_01
Patent number
US04071516

Reaction notes

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