Potassium Hydroxide → 2,3,4,5-Tetrahydro-1,4-benzoxazepin-5-one

HRID 1946632Notes

Reaction equation

HRID 1946632 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[N-:12]=[N+]=[N-].[Na+].[OH-].[K+]>S(=O)(=O)(O)O>[O:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4](=[O:11])[NH:12][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 33557Sodium AzideHCID 68110Chromanone

Product 1

HCID 3406292,3,4,5-Tetrahydro-1,4-benzoxazepin-5-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

The chroman-4-one (5.0 g, 33.8 mmol) was dissolved in sulfuric acid (10 mL) and the mixture was cooled at 0 oC. Sodium azide (2.88 g, 44.3 mmol) was added portionwise followed by some sulfuric acid (5 mL). The reaction mixture was stirred at room temperature over night. The mixture was then pour into ice-water and basified to pH=7 with potassium hydroxide pellets. This aqueous layer was extracted with ether (twice).

Workup

  1. temperaturethe mixture was cooled at 0 oC
  2. extractionThis aqueous layer was extracted with ether (twice)

Sources & evidence

ORD record
ord-88a9b647d76b4d0aa3e7a773eadd29f4
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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