Water → 10,11-Dihydrodibenzo(b,f)(1,4)oxazepine

HRID 477445Notes

Reaction equation

HRID 477445 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1[C:12]2[C:13](=O)[NH:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[O:17][C:11]=2[CH:10]=[CH:9][CH:8]=1.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH:7]1[C:12]2[CH2:13][NH:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[O:17][C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 72374O-(o-Aminophenoxy)benzoic acid lactamHCID 21226445Aluminium lithium hydride

Product 1

HCID 64893310,11-Dihydrodibenzo(b,f)(1,4)oxazepineYield 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a one liter three neck flask (argon atmosphere) was placed 50 ml of dry THF and 7.97 g (0.21 mole) of LAH. The suspension was stirred and a warm suspension of 29.57 g (0.14 mole) of 10,11-dihydro dibenz[b,f][1,4]oxazepine-11-one (Aldrich) in 500 ml of THF was added in a slow stream. The reaction mixture was stirred and heated to reflux for 3 hr. The reaction mixture was cooled and cautiously treated with 15 ml of water and 15 ml of saturated sodium sulfate solution. The mixture was stirred and heated to reflux for one hr. The solids were removed by filtration and washed with THF. The filtrate was concentrated to dryness to give 26.90 g of an oil that crystallized on standing. The nearly pure crystalline product was used in the next step without further purification.

Workup

  1. additionwas added in a slow stream
  2. stirringThe reaction mixture was stirred
  3. temperatureheated
  4. temperatureto reflux for 3 hr
  5. temperatureThe reaction mixture was cooled
  6. stirringThe mixture was stirred
  7. temperatureheated
  8. temperatureto reflux for one hr
  9. customThe solids were removed by filtration
  10. washwashed with THF
  11. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-81cb25eca54644d9be8c65a825ca28b0
Source dataset
uspto-grants-1989_12
Patent number
US04888335

Reaction notes

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