Chloral → 1,2-Dihydro-2-trichloromethylquinazolin-4-one

HRID 2286847Notes

Reaction equation

HRID 2286847 reaction equation
Cl.[C:2]([NH2:11])(=[O:10])[C:3]1[C:4](=[CH:6][CH:7]=[CH:8][CH:9]=1)[NH2:5].O=[CH:13][C:14]([Cl:17])([Cl:16])[Cl:15]>>[Cl:15][C:14]([Cl:17])([Cl:16])[CH:13]1[NH:11][C:2](=[O:10])[C:3]2[C:4](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:5]1

Participants

3

Reactant 2

HCID 6407Chloral2×HCID 23509772Anthranilamide hydrochloride

Product 1

HCID 133419081,2-Dihydro-2-trichloromethylquinazolin-4-one

Procedure

Anthranilamide hydrochloride (63.5 g.) was heated under reflux with anhydrous chloral (650 ml.) for three hours. The resulting solution was evaporated to dryness, and the residue was triturated with toluene (700 ml.) to give a yellow product containing one mole of chloral. This was removed by boiling the product with methanol (2 l.) for 15 minutes, cooling the solution and filtering. The filtrate was concentrated to half its volume, and allowed to cool, to produce 1,2-dihydro-2-trichloromethylquinazolin-4-one, m.p. 201°-202° C.

Workup

  1. customThe resulting solution was evaporated to dryness
  2. customthe residue was triturated with toluene (700 ml.)
  3. customto give a yellow product
  4. customThis was removed
  5. customfor 15 minutes
  6. temperaturecooling the solution
  7. filtrationfiltering
  8. concentrationThe filtrate was concentrated to half its volume
  9. temperatureto cool

Sources & evidence

ORD record
ord-4507f703206e4e119f5f30c9fdc0c5ae
Source dataset
uspto-grants-1981_05
Patent number
US04268510

Reaction notes

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