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

HRID 894193Notes

Reaction equation

HRID 894193 reaction equation
Cl[C:2]([C:4]1[CH:19]=[CH:18][C:7]2[O:8][CH2:9][C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[C:12](=[O:13])[C:6]=2[CH:5]=1)=[O:3].[NH3:20]>O1CCCC1>[O:13]=[C:12]1[C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[CH2:9][O:8][C:7]2[CH:18]=[CH:19][C:4]([C:2]([NH2:20])=[O:3])=[CH:5][C:6]1=2

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 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 8028TetrahydrofuranSolvent2×

Procedure

Dissolve the acid chloride from Step A in 20 ml. of dry tetrahydrofuran and add this solution dropwise with stirring to a cooled (ice-bath) saturated solution of ammonia in 60 ml. of tetrahydrofuran. Pass ammonia through the reaction mixture simultaneously for 15 minutes. Stir at room temperature for an additional 15 minutes and evaporate the reaction mixture to dryness. Add a mixture of 12 ml. of ethanol and 60 ml. of water to the residue and stir at room temperature for an additional 30 minutes. Separate the solid by filtration and wash with water, then with ethanol and then with ether. Dry in vacuo to obtain the title product.

Workup

  1. stirringStir at room temperature for an additional 15 minutes
  2. customevaporate the reaction mixture to dryness
  3. additionAdd
  4. additiona mixture of 12 ml
  5. stirringof water to the residue and stir at room temperature for an additional 30 minutes
  6. customSeparate the solid
  7. filtrationby filtration
  8. washwash with water
  9. customDry in vacuo

Sources & evidence

ORD record
ord-273c4663703e4349988802136b904ff6
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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