Sulfuric Acid → 5H-Dibenz(b,e)azepine-6,11-dione

HRID 2035416Notes

Reaction equation

S(=O)(=O)(O)O.[CH:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:21])[C:10]=2[CH:9]=[CH:8][CH:7]=1.[N-:22]=[N+]=[N-].[Na+]>ClCCl>[CH:6]1[C:19]2[C:18](=[O:20])[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11](=[O:21])[NH:22][C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of concentrated sulfuric acid (25.2 mL) and DCM (dichloromethane) (8.4 mL) was cooled to 0° C., anthraquinone (1) (5 g, 24 mmol) was added, then sodium azide (1.84 g, 28.3 mmol) was added in small portions over a 1 h period at 0-5° C. The reaction mixture stirred overnight at room temperature and then poured into ice water (300 mL). The product was filtered off, washed with water till acid-free and dried to give 5H-dibenzo[b,e]azepine-6,11-dione (2) as a white solid (5.3 g, 100%). Data: (m/z)=224 (M+H)+.

Workup

filtrationThe product was filtered off
washwashed with water till acid-free and
customdried

Sources & evidence

ORD record: ord-9354e0aee4c6421d89a83d765fb88b61
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575152B2

Reaction notes

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