Sulfuric Acid → 2,3,4,5-Tetrahydro-1,4-benzoxazepin-5-one

HRID 2296610

Reaktionsgleichung

Reaktionsgleichung von HRID 2296610
[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+].S(=O)(=O)(O)O.[OH-].[NH4+]>C(O)(=O)C>[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

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 33557Sodium AzideHCID 68110Chromanone

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To 4-chromanone (50 g, 340 mmol) in acetic acid (670 ml) was added sodium azide (66.31 g, 1.02 mol) and conc. sulfuric acid (100 ml) dropwise at 0° C. The mixture was heated to 50° C. for 4 h and then cooled to room temperature. The mixture was poured onto ice (1 l) and basified with conc. ammonium hydroxide. The mixture was stirred for 24 h and the solids were collected by filtration (30.43 g, 55%), MSm/z 164 [M+H]+.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. additionThe mixture was poured onto ice (1 l)
  3. filtrationthe solids were collected by filtration (30.43 g, 55%), MSm/z 164 [M+H]+

Quellen und Nachweise

ORD-Eintrag
ord-03f9efa86db84893bb5663712dff59b7
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06489322B1

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