1,1-Dichloroethane → 4-chlorobenzo[g]quinazoline

HRID 1249740Notes

Reaction equation

HRID 1249740 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH:9]=2)[C:4](=O)[NH:3][CH:2]=1.C=CC1C=CC=CC=1.[Cl:24]C(Cl)C>C(Cl)(Cl)(Cl)Cl>[Cl:24][C:4]1[C:5]2[C:10](=[CH:9][C:8]3[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=3[CH:6]=2)[N:1]=[CH:2][N:3]=1

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 7501StyreneHCID 135518939benzo[g]quinazolin-4(3H)-one

Product 1

HCID 110638054-chlorobenzo[g]quinazoline

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
22.5 °C

Procedure

A mixture of 3H-benzo[g]quinazolin-4-one (1.00 g, 5.07 mmol) and styrene-bound triphenylphosphine (2.53 g (approx. 3 mmoles/g), 7.61 mmol) in 15 mL dichloroethane and 15 mL carbon tetrachloride was heated to reflux for 1 hour, cooled to ambient temperature (20-25° C.) and filtered. Solvents were removed in vacuo to give 4-Chloro-benzo[g]quinazoline: 0.3881 g (36%); 1H NMR (DMSO-d6) δ7.63-7.71 (2H,m), 8.10 (1H, d, J=10 Hz), 8.28 (1H, d, J=10 Hz), 8.32 (1H, s), 8.69 (1H, s), 8.82 (1H, s).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. filtrationfiltered
  4. customSolvents were removed in vacuo

Sources & evidence

ORD record
ord-c662fa07a967497d8f5c41b2683f3cd0
Source dataset
uspto-grants-2002_01
Patent number
US06335344B1

Reaction notes

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