Chlorine → 2-Chloro-5H-dibenzo[b,e]azepine-6,11-dione

HRID 1938213Notes

Reaction equation

HRID 1938213 reaction equation
[Cl:1]Cl.[CH:3]1[C:13]2[C:12](=[O:14])[C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[C:9](=[O:19])[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1>C(O)(=O)C>[Cl:1][C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:9](=[O:19])[C:10]3[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=3[C:12](=[O:14])[C:13]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24526ChlorineHCID 708365H-Dibenz(b,e)azepine-6,11-dione

Product 1

HCID 134665322-Chloro-5H-dibenzo[b,e]azepine-6,11-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Chlorine gas is bubbled into a mixture (partial suspension) of 1.0 g (450 mmol) of 5H-dibenz[b,e]-azepine-6,11-dione in 50 ml of glacial acetic acid. The temperature of the mixture rises to 38° C. On standing, as the temperature of the solutions decreases, a white solid precipitates. The mixture is filtered to give 0.40 g of solid (mixture of starting material and product in ratio of 1:8). The filtrate on standing gives 0.10 g of product as crystals, m.p. 289°-293° C.

Workup

  1. customrises to 38° C
  2. customa white solid precipitates
  3. filtrationThe mixture is filtered

Sources & evidence

ORD record
ord-c66a22a8979c475d96f9bfe74474bea6
Source dataset
uspto-grants-1997_12
Patent number
US05693635

Reaction notes

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