Ammonia → HCID 13055167, compound

HRID 223744Notes

Reaction equation

HRID 223744 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:10]=1[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19])=O.[NH3:25]>C(O)C>[Br:24][C:21]1[CH:22]=[CH:23][C:9]2[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[CH2:2][N:25]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:10]=2[CH:20]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 20468881HCID 20468881, compound

Product 1

HCID 13055167HCID 13055167, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The solution of 5.4 g of 2-(o-bromomethylphenyl)-5-bromo-2'-fluorobenzophenone in 10 ml of ethanol is added slowly to the solution of 150 ml of saturated ethanolic ammonia while stirring at room temperature. After 2 days the mixture is evaporated, the residue taken up in methylene chloride and the solution washed with aqueous sodium carbonate. The organic layer is dried, evaporated and 5 g of the residue chromatographed on 50 g of silica gel, using first toluene, then toluene-diethyl ether (9:1) as the eluent. The later fraction is evaporated and the residue crystallized from hexane to yield the 9-bromo-7-(o-fluorophenyl)-5H-dibenz[c,e]azepine melting at 104°-105°.

Workup

  1. customAfter 2 days the mixture is evaporated
  2. washthe solution washed with aqueous sodium carbonate
  3. customThe organic layer is dried
  4. customevaporated
  5. custom5 g of the residue chromatographed on 50 g of silica gel
  6. customThe later fraction is evaporated
  7. customthe residue crystallized from hexane

Sources & evidence

ORD record
ord-53caaee7a476410db3f9160d13984f3a
Source dataset
uspto-grants-1982_10
Patent number
US04356176

Reaction notes

Loading…