HCID 13341964, compound → HCID 13341940, compound

HRID 2286870Notes

Reaction equation

HRID 2286870 reaction equation
O[CH:2]([NH:7][C:8](=[O:20])[C:9]1[C:10](=[CH:12][CH:13]=[C:14]([C:16]([O:18]C)=[O:17])[CH:15]=1)[NH2:11])[C:3]([Cl:6])([Cl:5])[Cl:4]>S(=O)(=O)(O)O>[O:20]=[C:8]1[C:9]2[C:10](=[CH:12][CH:13]=[C:14]([C:16]([OH:18])=[O:17])[CH:15]=2)[NH:11][CH:2]([C:3]([Cl:6])([Cl:5])[Cl:4])[NH:7]1

Participants

3

Reactant 1

HCID 13341964HCID 13341964, compound

Product 1

HCID 13341940HCID 13341940, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

N-(1-hydroxy-2,2,2-trichloroethyl)-5-methoxycarbonylanthranilamide (5 g.) and concentrated sulphuric acid (100 ml.) were heated together on a steam bath for 15 minutes, cooled, and poured onto a minimum quantity of ice. The precipitate thus formed was filtered off, dried and dissolved in hot ethanol (300 ml.). The ethanol solution was concentrated to 20 ml. and the solid produced was filtered off and discarded. The filtrate was further concentrated to 10 ml. and the product thus obtained was filtered off, dried and crystallised from glacial acetic acid/water, 1:1, to give 1,2-dihydro-4-oxo-2-trichloromethylquinazoline-6-carboxylic acid, m.p. > 280° C.

Workup

  1. temperaturecooled
  2. additionpoured onto a minimum quantity of ice
  3. customThe precipitate thus formed
  4. filtrationwas filtered off
  5. customdried
  6. dissolutiondissolved in hot ethanol (300 ml.)
  7. concentrationThe ethanol solution was concentrated to 20 ml
  8. customand the solid produced
  9. filtrationwas filtered off
  10. concentrationThe filtrate was further concentrated to 10 ml
  11. customand the product thus obtained
  12. filtrationwas filtered off
  13. customdried
  14. customcrystallised from glacial acetic acid/water, 1:1

Sources & evidence

ORD record
ord-68034c5e965e4a72b6a3fb54817d28de
Source dataset
uspto-grants-1981_05
Patent number
US04268510

Reaction notes

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