Water → HCID 20366415, compound

HRID 616889Notes

Reaction equation

HRID 616889 reaction equation
[Cl:1][C:2]1(Cl)[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[Cl:20].N12CCCCC1C=NCCC2.O>CN(C)C=O>[Cl: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[C:3]=1[Cl:20]

Participants

5

Reactant 3

HCID 962WaterHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 20366406HCID 20366406, compound

Product 1

HCID 20366415HCID 20366415, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 8.33 g of crude 10,11-dihydro-10,10,11-trichloro-5H-dibenz[b,f]azepine-5-carboxamide in 35 ml of dimethyl formamide is treated at 0°-10° C with 9.1 ml (0.61 mole) of 1,5-diazabicyclo[5.4.0]undec-5-ene and stirred for 1 hour at room temperature. The brown 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. The crude product is chromatographed over silica gel (particle size: 0.063-0.2 mm) with ethyl acetate as eluant. The homogeneous fractions are combined, concentrated by evaporation and recrystallised from ethyl acetate to yield 10,11-dichloro-5H-dibenz[b,f]azepine-5-carboxamide which melts at 265°-270° C.

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
  5. customThe crude product is chromatographed over silica gel (particle size: 0.063-0.2 mm) with ethyl acetate as eluant
  6. concentrationconcentrated by evaporation
  7. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-e7f68c3a78ec422c86ac98df2cbcbb69
Source dataset
uspto-grants-1978_02
Patent number
US04076812

Reaction notes

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