Acetyl chloride → HCID 606375, compound

HRID 1977671Notes

Reaction equation

HRID 1977671 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH:5]1[C:15]2[CH:14]=[CH:13][C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1>C(Cl)(Cl)Cl>[C:1]([N:10]1[C:11]2[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=2[CH:13]=[CH:14][C:15]2[CH:5]=[CH:6][CH:7]=[CH:8][C:9]1=2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 9212Dibenz(b,f)azepine

Product 1

HCID 606375HCID 606375, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Acetyl chloride (11.0 ml) was added to a chloroform (250 ml) solution of 5H-dibenzo[b,f]azepine (25.0 g) under ice-cooling. The solution was heated under reflux for 30 minutes, then allowed to cool. The organic phase was washed with a saturated sodium bicarbonate aqueous solution, water, and saturated brine; dried over anhydrous sodium sulfate; and filtered. The filtrate was concentrated, and the resulting residue was recrystallized from ethyl acetate-hexane to obtain N-acetyl-5H-dibenzo[b,f]azepine (28.6 g; yield, 94%) as a white solid.

Workup

  1. temperaturecooling
  2. temperatureThe solution was heated
  3. temperatureunder reflux for 30 minutes
  4. temperatureto cool
  5. washThe organic phase was washed with a saturated sodium bicarbonate aqueous solution, water, and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationand filtered
  8. concentrationThe filtrate was concentrated
  9. customthe resulting residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d2b63daf797549be9d6eb7565d5be6ee
Source dataset
uspto-grants-2001_05
Patent number
US06235730B1

Reaction notes

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