Sulfuric Acid → N-[2-(3,9-dioxo-1,2,3,9,10,11-hexahydro-6H-dicyclopenta[c,g]carbazol-6-yl)ethyl]-2-nitrobenzenesulfonamide

HRID 514776Notes

Reaction equation

S(=O)(=O)(O)O.Cl[CH2:7][CH2:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH2:29][CH2:30][NH:31][S:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[N+:41]([O-:43])=[O:42])(=[O:34])=[O:33])[C:16]3[C:21]([C:22]=2[CH:23]=1)=[CH:20][C:19]([C:24](=[O:28])[CH2:25][CH2:26]Cl)=[CH:18][CH:17]=3)=[O:10]>C(Cl)Cl.C(OCC)(=O)C>[O:10]=[C:9]1[C:11]2[CH:12]=[CH:13][C:14]3[N:15]([CH2:29][CH2:30][NH:31][S:32]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[N+:41]([O-:43])=[O:42])(=[O:34])=[O:33])[C:16]4[CH:17]=[CH:18][C:19]5[C:24](=[O:28])[CH2:25][CH2:26][C:20]=5[C:21]=4[C:22]=3[C:23]=2[CH2:7][CH2:8]1

Participants

Conditions

Temperature: 90 °C

Procedure

Sulfuric acid (200 mL) was heated to 40° C. Then, compound 57 (18.47 g, 32.12 mmol) was added in portions. The mixture was heated to 90° C. and kept at this temperature for 1.5-2 h (TLC monitoring, eluent: CH2Cl2-ethyl acetate, 4:1). The resulting mixture was poured onto ice. The grey precipitate was filtered off, washed on a filter with a mixture of CHCl3-MeOH (4:1). The remaining precipitate (on a filter) was recrystallized with DMF, washed with CH3CN and ether. Yield of pure 58: 2.2 g (14%).

Workup

additionThe resulting mixture was poured onto ice
filtrationThe grey precipitate was filtered off
washwashed on
filtrationa filter with a mixture of CHCl3-MeOH (4:1)
filtrationThe remaining precipitate (on a filter)
customwas recrystallized with DMF
washwashed with CH3CN and ether

Sources & evidence

ORD record: ord-8862759a8e3a4395a89223a96bf3d133
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108916B2

Reaction notes

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