Hydrochloric Acid → 5-(4-Nitrobenzoyl)-6 7-dihydro-5H-dibenz[b,d]azepine

HRID 355845Notes

Reaction equation

HRID 355845 reaction equation
[N+:1]([C:4]1[CH:28]=[CH:27][C:7]([C:8]([N:10]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2I)[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2I)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl>CC1N(C(N(C)C)=O)C1.[Cu]>[N+:1]([C:4]1[CH:28]=[CH:27][C:7]([C:8]([N:10]2[CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]2=3)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54109817N-(4-nitrobenzoyl)-N-(2-iodophenyl)-2-iodobenzeneethylamine

Product 1

HCID 540065545-(4-Nitrobenzoyl)-6 7-dihydro-5H-dibenz[b,d]azepineYield 96.5%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 11007919N,N,2-trimethylaziridine-1-carboxamideSolvent

Procedure

To a solution of 0.90 g of N-(4-nitrobenzoyl)-N-(2-iodophenyl)-2-iodobenzeneethylamine in 10 ml of N,N-dimethylpropyleneurea (DMPU) is added 1.91 g of "activated" copper bronze. The mixture is stirred and heated at 195° for 2 days, cooled and slowly dropped into 100 ml of 0.5N HCl with stirring. The precipitate is filtered, washed with H2O and air dried (1.0 g of solid). The solid is extracted with ethyl acetate to give 0.50 g of solid. Chromatography on thick layer silica gel plates with ethyl acetate-hexane (1:2) as solvent gives 0.15 g of yellow solid.

Workup

  1. temperatureheated at 195° for 2 days
  2. temperaturecooled
  3. stirringwith stirring
  4. filtrationThe precipitate is filtered
  5. washwashed with H2O and air
  6. dry with materialdried (1.0 g of solid)
  7. extractionThe solid is extracted with ethyl acetate

Sources & evidence

ORD record
ord-596659baef374971b9249e4b7a82b3cc
Source dataset
uspto-grants-1998_11
Patent number
US05834461

Reaction notes

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