Water → HCID 20366413, compound

HRID 616887Notes

Reaction equation

HRID 616887 reaction equation
Br[CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[C:5]2[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=2[CH:3]1[Br:23].N12CCCCC1C=NCCC2.O>CN(C)C=O>[Br:23][C:3]1[C:4]2[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=2[N:6]([C:13](=[O:18])[C:14]([F:16])([F:17])[F:15])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 20366416HCID 20366416, compound

Product 1

HCID 20366413HCID 20366413, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 138.1 g of 10,11-dibromo-10,11-dihydro-5-(trifluoroacetyl)-5H-dibenz[b,f]azepine in 580 ml of dimethyl formamide is treated at 0°-10° C with 114.5 ml of 1,5-diazabicyclo[5.4.0]undec-5-ene and stirred for 1 hour at the same temperature. The dark solution is then poured into a mixture of water and ice and the resultant suspension is extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated by evaporation, to yield crude, syrupy 10-bromo-5-(trifluoroacetyl)-5H-dibenz[b,f]azepine which is directly processed further.

Workup

  1. extractionthe resultant suspension is extracted with ethyl acetate
  2. washThe organic phase is washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-441be515f0554bb392d505f5d9c1a74f
Source dataset
uspto-grants-1978_02
Patent number
US04076812

Reaction notes

Loading…