Sodium Azide → 8-Chloro-3-methoxy-1H-1-benzazepine-2,5-dione
Reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:15])[CH:7]=[C:8]([O:13][CH3:14])[C:9]2=[O:12])=[CH:4][CH:3]=1.FC(F)(F)S(O)(=O)=O.[N-:24]=[N+]=[N-].[Na+]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:15])[CH:7]=[C:8]([O:13][CH3:14])[C:9](=[O:12])[NH:24][C:10]=2[CH:11]=1Participants
Procedure
7-Chloro-2-methoxy-1,4-naphthoquinone (14.74 g) was added to trifluoromethanesulfonic acid (153 mL) chilled in an ice bath, and sodium azide (4.74 g) was added. The reaction mixture was maintained in an ice bath for 0.33 hour then allowed to warm to room temperature and maintained thus for 90 hours. The reaction mixture was recooled in an ice bath, and an additional portion of sodium azide (2.15 g) was added. After 0.08 hour the mixture was allowed to warm to room temperature for 19 hours. The reaction mixture was then poured into ice cold aqueous sodium bicarbonate (2.3 L). The resulting precipitate was filtered, washed (water) and dried under vacuum (25° C., 15 Pa) to give a tan solid (13.83 g). The solid was recrystallized from hot dimethylformamide (300 mL) and dried under vacuum (25° C., 15 Pa) to give the benz[b]azepine as a light tan solid (8.12 g); mp 340°-342° C. (dec). Analysis for C11H8ClNO3 : Calculated: C, 55.60; H, 3.39; N, 5.89; Found: C, 55.35; H, 3.38; N, 6.07.
Workup
- temperaturechilled in an ice bath
- temperatureThe reaction mixture was maintained in an ice bath for 0.33 hour
- temperaturemaintained thus for 90 hours
- customThe reaction mixture was recooled in an ice bath
- temperatureto warm to room temperature for 19 hours
- filtrationThe resulting precipitate was filtered
- washwashed (water)
- customdried under vacuum (25° C., 15 Pa)
Sources & evidence
- ORD record
- ord-e672eda42c9f4b4cb65ecbac0ceb12b6
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05712272
Reaction notes
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