Water → 10-Bromocarbamazepine

HRID 616886Notes

Reaction equation

HRID 616886 reaction equation
[Br:1][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13]([NH2:15])=[O:14])[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[CH:3]1Br.N12CCCC1=NCCC2.O>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13]([NH2:15])=[O:14])[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 606479HCID 606479, compound

Product 1

HCID 16288610-Bromocarbamazepine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

With cooling at 5°-10° C, 12 g (app. 0.03 mole) of the crude 10,11-dibromo-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide obtained according to (a) are suspended in 35 ml of dimethyl formamide. With stirring, 10 g (app. 0.08 mole) of 1,5-diazabicyclo[4.3.0]non-5-ene are added dropwise at 5°-10° C. Stirring is continued for 2 hours at 25° C and a new precipitate forms. The reaction mixture is then heated for 10 minutes to 90°-100° C and, after it has cooled, poured onto a mixture of water and ice and the organic phase is dissolved in ethyl acetate. The aqueous phase is then separated and the organic phase is washed with water, dried over calcium chloride and evaporated in a water jet vacuum. The residue is crystallised from 30 ml of acetonitrile to yield light green 10-bromo-5-H-dibenz[b,f]azepine-5-carboxamide of m.p. 168°-170° C.

Workup

  1. temperatureWith cooling at 5°-10° C
  2. stirringStirring
  3. temperatureThe reaction mixture is then heated for 10 minutes to 90°-100° C
  4. temperatureafter it has cooled
  5. customThe aqueous phase is then separated
  6. washthe organic phase is washed with water
  7. dry with materialdried over calcium chloride
  8. customevaporated in a water jet vacuum
  9. customThe residue is crystallised from 30 ml of acetonitrile

Sources & evidence

ORD record
ord-063a1635391f43e5b582ad114db9fb5d
Source dataset
uspto-grants-1978_02
Patent number
US04076812

Reaction notes

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