Phosphorus oxychloride → 4-Chloro-6-iodo-2-(trifluoromethyl)quinazoline

HRID 2257512Notes

Reaction equation

HRID 2257512 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[NH:6][C:5]2=O.O=P(Cl)(Cl)[Cl:19]>>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[N:6]=[C:5]2[Cl:19]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135990571HCID 135990571, compound

Product 1

HCID 190749504-Chloro-6-iodo-2-(trifluoromethyl)quinazoline

Procedure

6-iodo-2-trifluoromethyl-3H-quinazolin-4-one (3.1 g, 9.1 mmole) was mixed with 20 mL of POCl3, heated to reflux for 3 h, removed most of unreacted POCl3 under vacuo. The residue was extracted with 15 mL of NaHCO3 (sat) and 200 mL of ether, ether layer was dried with MgSO4 and concentrated to give the light yellow solid 3.05 g, mp 145°-146° C., MS (CI): m/z 359 (MH)+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. customremoved most of unreacted POCl3 under vacuo
  4. extractionThe residue was extracted with 15 mL of NaHCO3 (sat) and 200 mL of ether, ether layer
  5. dry with materialwas dried with MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1c2c0e41765540e09c1d2ad3da6ceec5
Source dataset
uspto-grants-1997_08
Patent number
US05658902

Reaction notes

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