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

HRID 718102

Reaction equation

HRID 718102 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×

Conditions

Temperature
0 °C

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° C. 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. extractionThis aqueous layer was extracted with ether (twice)

Sources & evidence

ORD record
ord-c15779cfa74d436daa5d0b80ddb66e44
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Linked notes

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