Pyridine → HCID 606375, compound

HRID 1680663Notes

Reaction equation

HRID 1680663 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[C:22](Cl)(=[O:24])[CH3:23]>C1C=CC=CC=1>[C:22]([N:6]1[C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[CH:9]=[CH:10][C:11]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 9212Dibenz(b,f)azepine

Product 1

HCID 606375HCID 606375, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a 500 ml round bottom flask fitted with a stirrer, dropping funnel and calcium chloride drying tube was placed recrystallized dibenz[b,f]azepine (33.5 g, 0.173 moles), 200 ml of anhydrous benzene and pyridine (13.6 g, 0.173 moles). Acetyl chloride (~12.3 ml) was then added dropwise to the mixture. A white precipitate formed with disappearance of orange color. After 3 to 4 hours of stirring, the reaction mixture was extracted with three 100 ml portions of 10% hydrochloric acid or until the extract remained acidic. The organic phase was washed with 5% Na2CO3 in water, dried over anhydrous magnesium sulfate, filtered and concentrated. Crystallization from a hexane-chloroform mixture afforded 49 g of 5-acetyl-5H-dibenz[b,f]azepine, m.p. ~121°.

Workup

  1. customIn a 500 ml round bottom flask fitted with a stirrer
  2. customA white precipitate formed with disappearance of orange color
  3. extractionthe reaction mixture was extracted with three 100 ml portions of 10% hydrochloric acid or until the extract
  4. washThe organic phase was washed with 5% Na2CO3 in water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customCrystallization from a hexane-chloroform mixture

Sources & evidence

ORD record
ord-9efad3a9b3c74a81b5aeeba53138b4a1
Source dataset
uspto-grants-1981_06
Patent number
US04275160

Reaction notes

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