Sodium Methoxide → HCID 20450024, compound

HRID 358059Notes

Reaction equation

HRID 358059 reaction equation
Br[C:2]1[N:6]2[C:7]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:8]=3[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])=[CH:10][CH2:11][C:5]2=[N:4][N:3]=1.C[O-:25].[Na+]>CO>[Cl:23][C:20]1[CH:21]=[CH:22][C:7]2[N:6]3[C:2](=[O:25])[NH:3][N:4]=[C:5]3[CH2:11][CH:10]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[C:8]=2[CH:19]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 20449986HCID 20449986, compound

Product 1

HCID 20450024HCID 20450024, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.9 g of 1-bromo-8-chloro-6-(2-fluorophenyl)-4H-s-triazolo[4,3-a][1]benzazepine are suspended in 90 ml of methanol and treated with 1.62 of g of sodium methylate. The mixture is heated to boiling under reflux for 20 hours and then evaporated. The residue, which contains predominantly 8-chloro-6-(2-fluorophenyl)-1-methoxy-4H-s-triazolo[4,3-a][1]benzazepine, is heated to boiling under reflux for 4.5 hours in 100 ml of 48% hydrobromic acid. The mixture is diluted with water, made weakly alkaline with sodium carbonate and extracted with methylene chloride. The methylene chloride solution is evaporated and the residue is chromatographed on 120 g of aluminium oxide (activity grade III). Impurities are separated by elution with benzene/chloroform (9:1 to 1:4). By elution with chloroform which contains 1% to 10% methanol and two-fold recrystallization of the resulting material from benzene there is obtained 8-chloro-6-(2-fluorophenyl)-2,4-dihydro-1H-s-triazolo[4,3-a][1]benzazepin-1-one of melting point 223°-225°.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 20 hours
  3. customevaporated
  4. temperatureis heated
  5. temperatureunder reflux for 4.5 hours in 100 ml of 48% hydrobromic acid
  6. additionThe mixture is diluted with water
  7. extractionextracted with methylene chloride
  8. customThe methylene chloride solution is evaporated
  9. customthe residue is chromatographed on 120 g of aluminium oxide (activity grade III)
  10. customImpurities are separated by elution with benzene/chloroform (9:1 to 1:4)
  11. washBy elution with chloroform which
  12. custom1% to 10% methanol and two-fold recrystallization of the resulting material from benzene

Sources & evidence

ORD record
ord-c2bb3700144c4e0fb84ea1c968e196ca
Source dataset
uspto-grants-1984_08
Patent number
US04464300

Reaction notes

Loading…