Phosphorus oxychloride → 6-Iodo-4-chloro-2-trichloromethyl quinazolin

HRID 2257509Notes

Reaction equation

HRID 2257509 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]([Cl:15])([Cl:14])[Cl:13])[NH:6][C:5]2=O.O=P(Cl)(Cl)[Cl:19]>C1(C)C=CC=CC=1>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([Cl:15])([Cl:14])[Cl:13])[N:6]=[C:5]2[Cl:19]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 190749436-Iodo-2-trichloromethyl-1,2-dihydro-quinazolin-4-one

Product 1

HCID 6329086-Iodo-4-chloro-2-trichloromethyl quinazolin

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 6-iodo-2-trichloromethyl-1,2-dihydro-quinazolin-4-one (38.9 g=100 mmol) in POCl3 (500 mL) was heated to reflux for 12 hours. The homogeneous solution was cooled and excess POCl3 was distilled under vacuum. Viscous oil obtained was poured over crushed ice and triturated vigorously to give grey solid, which was dissolved in toluene (200 mL), filtered and evaporated under vacuo to give off-white crystalline solid. Mp 154°-155° C. Elemental Analysis: Calculated for C9H3Cl4IN2, C: 26.50, H, 0.74, N: 6.87; Found: C: 26.15, H: 0.79, N. 6.68.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. temperatureThe homogeneous solution was cooled
  4. distillationexcess POCl3 was distilled under vacuum
  5. customViscous oil obtained
  6. additionwas poured
  7. customover crushed ice
  8. customtriturated vigorously
  9. customto give grey solid, which
  10. filtrationfiltered
  11. customevaporated under vacuo
  12. customto give off-white crystalline solid

Sources & evidence

ORD record
ord-25c0ebfdce6146d4b0a6d1c12dbdd05f
Source dataset
uspto-grants-1997_08
Patent number
US05658902

Reaction notes

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