Ammonia → 6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-carboamide

HRID 1982372Notes

Reaction equation

HRID 1982372 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([C:17](Cl)=[O:18])=[CH:16][C:3]1=2.[NH3:20]>O1CCCC1>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([C:17]([NH2:20])=[O:18])=[CH:16][C:3]1=2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 134560052-Chlorocarbonyl-6,11-dihydro-11-oxodibenz[b,e]oxepin

Product 1

HCID 124468236,11-Dihydro-11-oxodibenz[b,e]oxepin-2-carboamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The remaining half of the acid chloride IV was added to a mixture of 150 ml of concentrated ammonia and 150 ml of tetrahydrofuran. Then, the mixture was stirred at room temperature for three hours and concentrated under reduced pressure. The residue was vigorously stirred together with 300 ml of saturated aqueous solution of sodium bicarbonate and 100 ml of ether, and the solid was collected by filtration and dried to obtain 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-carboamide VIII in a quantitative yield. Recrystallization from methanol gave pure crystals having a melting point of 227°-228° C. IR spectrum (KBr tablet, cm-1): 3430, 3150, 1680, 1635, 1600, 1370.

Workup

  1. concentrationconcentrated under reduced pressure
  2. stirringThe residue was vigorously stirred together with 300 ml of saturated aqueous solution of sodium bicarbonate and 100 ml of ether
  3. filtrationthe solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-964c45345b2b4a7296b2a45afb0ef1fa
Source dataset
uspto-grants-1986_06
Patent number
US04596804

Reaction notes

Loading…