Pyridine → 10-acetyloxyimino-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide

HRID 361319Notes

Reaction equation

HRID 361319 reaction equation
[OH:1][N:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14]([NH2:16])=[O:15])[C:6]2[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=2[CH2:4]1.N1C=CC=CC=1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>ClCCl>[C:27]([O:1][N:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14]([NH2:16])=[O:15])[C:6]2[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=2[CH2:4]1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 85040065Bia-2-024

Product 1

HCID 5708406910-acetyloxyimino-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 0.5 g (1.87 mmol) of 10,11-dihydro-10-hydroxyimino-5H-dibenz[b,f]azepine-5-carboxamide in 25 mL of dichloromethane and 0.72 g (9.16 mmol) of pyridine was treated with 0.57 g (5.61 mmol) of acetic anhydride. The resulting mixture was stirred at room temperature overnight and then diluted with 10 mL of dichloromethane. The organic phase was extracted with 20 mL of 1M aqueous HCl, a saturated solution of NaHCO3 and brine, then dried by sodium sulphate. The solvent was then removed by evaporation under reduced pressure and the crude product was crystallised from a mixture of dichloromethane and ethyl acetate to give the desired product as white crystals of m.p. 175.8°-176.9° C.

Workup

  1. extractionThe organic phase was extracted with 20 mL of 1M aqueous HCl
  2. dry with materiala saturated solution of NaHCO3 and brine, then dried by sodium sulphate
  3. customThe solvent was then removed by evaporation under reduced pressure
  4. customthe crude product was crystallised from a mixture of dichloromethane and ethyl acetate

Sources & evidence

ORD record
ord-3b61c0bcfff9478eac46a65b37b5ca0e
Source dataset
uspto-grants-1999_02
Patent number
US05866566

Reaction notes

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