Azobisisobutyronitrile → 5-Bromo-4-chloro-5,6,7,8-tetrahydro-2-trifluoromethylquinazoline

HRID 2254125Notes

Reaction equation

HRID 2254125 reaction equation
[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[N:3]=1.[Br:16]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)Cl>[Br:16][CH:10]1[CH2:9][CH2:8][CH2:7][C:6]2[N:5]=[C:4]([C:12]([F:14])([F:15])[F:13])[N:3]=[C:2]([Cl:1])[C:11]1=2

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 19383098HCID 19383098, compound

Product 1

HCID 197441915-Bromo-4-chloro-5,6,7,8-tetrahydro-2-trifluoromethylquinazolineYield 58.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 17.63 g of 4-chloro-5,6,7,8,-tetrahydro-2-trifluoromethylquinazoline in 220 mL of chloroform was added 14.6 g of N-bromosuccinimide and 0.85 g of AIBN. The resulting reaction mixture was heated to reflux overnight under a nitrogen atmosphere. The reaction was cooled, filtered and all solvents were removed by evaporation. The residue was purified on a silica column (5% ethyl acetate in hexane) to yield 13.7 g (58%) of the required compound. This material was carried to the next step with no further purification.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux overnight under a nitrogen atmosphere
  4. temperatureThe reaction was cooled
  5. filtrationfiltered
  6. customall solvents were removed by evaporation
  7. customThe residue was purified on a silica column (5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-a288336c914e4140a52f3324b76cd515
Source dataset
uspto-grants-1993_08
Patent number
US05234936

Reaction notes

Loading…