Pyridine → HCID 57000167, compound

HRID 361321Notes

Reaction equation

HRID 361321 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.Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:31]([O:30][C:28]([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])[CH3:32]

Participants

6

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 85040065Bia-2-024

Product 1

HCID 57000167HCID 57000167, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 0.2 g (0.74 mmol) of 10,11-dihydro-10-hydroxyimino-5H-dibenz[b,f]azepine-5-carboxamide and 0.01 g (0.08 mmol) of 4-dimethylaminopyridine in 10 mL of dichloromethane and 0.29 g (3.7 mmol) of pyridine was added 0.28 g (2.6 mmol) of ethyl chloroformate dropwise. The resulting mixture was stirred at room temperature for 2 hours whereupon it was extracted with 20 mL of 1M aqueous HCl and a saturated solution of NaHCO3, then dried by sodium sulphate and filtered. The solvent was removed by evaporation under reduced pressure and the residue was crystallised from a mixture of dichloromethane and ethyl acetate to give white crystals of m.p. 188.9°-190° C.

Workup

  1. extractionwas extracted with 20 mL of 1M aqueous HCl
  2. dry with materiala saturated solution of NaHCO3, then dried by sodium sulphate
  3. filtrationfiltered
  4. customThe solvent was removed by evaporation under reduced pressure
  5. customthe residue was crystallised from a mixture of dichloromethane and ethyl acetate
  6. customto give white crystals of m.p. 188.9°-190° C.

Sources & evidence

ORD record
ord-69ab47045ce3482cb2f6091bafb7e80b
Source dataset
uspto-grants-1999_02
Patent number
US05866566

Reaction notes

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