Hydrochloric Acid → HCID 23333639, compound

HRID 904199Notes

Reaction equation

HRID 904199 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][N:6]1[CH2:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9](=[O:17])[C:8]2[CH:18]=[CH:19][CH:20]=[CH:21][C:7]1=2.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[C:1]([C:19]1[CH:20]=[CH:21][C:7]2[N:6]([CH3:5])[CH2:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[C:9](=[O:17])[C:8]=2[CH:18]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 18917171HCID 18917171, compound

Product 1

HCID 23333639HCID 23333639, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (8.5 g) was gradually added dropwise to a mixed liquid of 5,6-dihydro-5-methyl-11-oxodibenz[b,e]azepine (12 g), anhydrous aluminum chloride (21.5 g) and dried methylene chloride (200 ml) while stirring and cooling the liquid with ice. After the dropwise addition, the mixture was stirred for 30 minutes at room temperature, and was heated under refluxing for one hour. Immediately after the reaction, the reaction mixture was poured into a solution containing ice-water (1 kg) and conc. hydrochloric acid (50 ml) while stirring to separate the methylene chloride layer. This layer was washed with a 5% sodium hydrogencarbonate solution, then with water, and dried over magnesium sulfate. Thereafter, the solvent was distilled off, and the residue was recrystallized from methanol to afford the desired compound (13.2 g).

Workup

  1. temperaturecooling the liquid with ice
  2. additionAfter the dropwise addition
  3. stirringthe mixture was stirred for 30 minutes at room temperature
  4. temperaturewas heated
  5. temperatureunder refluxing for one hour
  6. customImmediately after the reaction
  7. additionthe reaction mixture was poured into a solution
  8. stirringwhile stirring
  9. customto separate the methylene chloride layer
  10. washThis layer was washed with a 5% sodium hydrogencarbonate solution
  11. dry with materialwith water, and dried over magnesium sulfate
  12. distillationThereafter, the solvent was distilled off
  13. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-9b8a36f3a0d245a6bd8fd56363d27a73
Source dataset
uspto-grants-1980_10
Patent number
US04230703

Reaction notes

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