Pyridine → Iminostilbene N-carbonylchloride

HRID 1603243Notes

Reaction equation

HRID 1603243 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:8]=[CH:7][C:5]=2[CH:6]=1.[Cl:16][C:17](Cl)([O:19]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1>ClCCl.C(OCC)(=O)C.CCCCCC>[CH:10]1[C:9]2[CH:8]=[CH:7][C:5]3[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=3[N:15]([C:17]([Cl:16])=[O:19])[C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 9212Dibenz(b,f)azepineHCID 94429Triphosgene

Product 1

HCID 182151Iminostilbene N-carbonylchlorideYield 247.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A solution of 2.8 g of iminostilbene (34) in 100 mL of dichloromethane was treated with 1.5 g of triphosgene followed by 3 mL of pyridine and stirred at room temperature overnight. Thin layer chromatography in 40% ethyl acetate-hexane indicated formation of one product. The reaction mixture was washed with water and concentrated in vaccuo. The residue was chromatographed on silica using 10% ether/dichloromethane to yield 3.2 g of 5H-dibenz[b,f]azepine-5-carbonylchloride (35) as an off-white powder. NMR, IR and MS data confirmed the compound identity.

Workup

  1. washThe reaction mixture was washed with water
  2. concentrationconcentrated in vaccuo
  3. customThe residue was chromatographed on silica using 10% ether/dichloromethane

Sources & evidence

ORD record
ord-b704e00485244b16be4d08b3af0c8cf8
Source dataset
uspto-grants-1999_11
Patent number
US05986094

Reaction notes

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