Ethanol → HCID 23333618, compound

HRID 904190Notes

Reaction equation

HRID 904190 reaction equation
[CH3:1][N:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5](=[O:13])[C:4]2[CH:14]=[C:15]([CH2:18][C:19]([O:21]C)=[O:20])[CH:16]=[CH:17][C:3]1=2.[Br:23]N1C(=O)CCC1=O.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C(Cl)(Cl)Cl>[Br:23][C:17]1[C:3]2[N:2]([CH3:1])[CH2:8][C:7]3[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=3[C:5](=[O:13])[C:4]=2[CH:14]=[C:15]([CH2:18][C:19]([OH:21])=[O:20])[CH:16]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 67184N-bromobutanimideHCID 23333585HCID 23333585, compound

Product 1

HCID 23333618HCID 23333618, compoundYield 10.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methyl 5,6-dihydro-5-methyl-11-oxodibenz[b,e]azepine-2-acetate (0.750 g) was dissolved in chloroform (10 ml), and N-bromosuccinimide (0.550 g) was added to the solution. The mixture was refluxed overnight, and cooled. The mixture was then washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give an oily material. A 10% sodium carbonate aqueous solution (15 ml) and ethanol (10 ml) were added to the oily material, and the mixture was refluxed overnight. The contents were concentrated to 1/3 the original volume under reduced pressure with heating. The concentrate was treated with activated carbon powder, and acidified with 10% HCl with ice cooling. The precipitated crystals were collected by filtration and recrystallized from acetone to afford 5,6-dihydro-4-bromo-5-methyl-11-oxodibenz[b,e]azepine-2-acetic acid (prismatic crystals, 0.100 g) having a melting point of 164°-167° C.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperaturecooled
  3. washThe mixture was then washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customto give an oily material
  7. temperaturethe mixture was refluxed overnight
  8. concentrationThe contents were concentrated to 1/3 the original volume under reduced pressure
  9. temperaturewith heating
  10. additionThe concentrate was treated with activated carbon powder
  11. filtrationThe precipitated crystals were collected by filtration
  12. customrecrystallized from acetone

Sources & evidence

ORD record
ord-8196ff4fe1b04992bce46a7557d5aa53
Source dataset
uspto-grants-1980_10
Patent number
US04230703

Reaction notes

Loading…