Benzophenone imine → HCID 59841036, compound

HRID 1910309Notes

Reaction equation

HRID 1910309 reaction equation
[NH2:1][CH2:2][C:3]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:11](=[O:19])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:20])[N:4]=1.[C:21](=N)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCCl>[C:21](=[N:1][CH2:2][C:3]1[N:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:11](=[O:19])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:20])[N:4]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 136809Benzophenone imineHCID 59841076HCID 59841076, compound

Product 1

HCID 59841036HCID 59841036, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A 100-mL, one-neck, round bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 2-aminomethyl-5-methyl-3-phenyl-3H-quinazolin-4-one (2.91 g, 11.0 mmol), benzhydrylideneamine (2.39 g, 13.2 mmol), and 1,2-dichloroethane (15 mL). The reaction mixture was heated at reflux for 4 h under nitrogen atmosphere and then cooled to ambient temperature. Concentration under reduced pressure followed by purification by column chromatography afforded the compound 162 as an orange solid. m.p. 49° C. (dec); 1H NMR (DMSO-d6) δ (ppm) 7.22-7.78 (m, 17H), 6.74 (m, 1H), 4.17 (s, 2H), 2.74 (s, 3H); m/z=430 (M+H). The reaction described above and compound 162 are shown below.

Workup

  1. customA 100-mL, one-neck, round bottomed flask equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 4 h under nitrogen atmosphere
  5. concentrationConcentration under reduced pressure
  6. customfollowed by purification by column chromatography

Sources & evidence

ORD record
ord-1f45b421548d48a3a89fe0e9ca1e239e
Source dataset
uspto-grants-2013_12
Patent number
USRE044638E1

Reaction notes

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