4-Hydrazinylbenzenesulfonamide hydrochloride → HCID 178514741, Verbindung

HRID 1935505Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1935505
[C:1]1(=[CH:5][C:6]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:7]=2[C:8](=O)[C:9](=[O:15])[NH:10]3)[CH2:4][CH2:3][CH2:2]1.IC1C=CC=C2C=1C(=O)C(=O)N2.C=C1CC=C1.[CH:34]1[C:39]([NH:40][NH2:41])=[CH:38][CH:37]=[C:36]([S:42]([NH2:45])(=[O:44])=[O:43])[CH:35]=1.Cl>>[C:1]1(=[CH:5][C:6]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:7]=2[C:8](=[N:41][NH:40][C:39]2[CH:38]=[CH:37][C:36]([S:42]([NH2:45])(=[O:43])=[O:44])=[CH:35][CH:34]=2)[C:9](=[O:15])[NH:10]3)[CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 4

HCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 106359514-Iodoindoline-2,3-dioneHCID 127320073-Methylidenecyclobut-1-eneHCID 219562954-cyclobutylidenemethyl-1H-indole-2,3-dione2×

Produkt 1

HCID 178514741HCID 178514741, VerbindungAusbeute 76 %

Versuchsvorschrift

By methods described in Procedure L, 4-cyclobutylidenemethyl-1H-indole-2,3-dione was prepared from 4-iodo-1H-indole-2,3-dione and methylene cyclobutene in 25% yield: 1H NMR (DMSO-d6): δ 2.08 (quintet, J=7.8 Hz, 2H), 2.91 (m, 2H), 3.06 (m, 2H), 6.67 (d, J=7.7 Hz, 1H), 6.94 (d, J=7.7 Hz, 1H), 6.96 (s, 1H), 7.47 (d, J=7.7 Hz, 1H), 11.00 (bs, 1H); APCI−MS m/z 211 (M−1)−. Condensation of 4-(cyclobutylidenemethyl)-1H-indole-2,3-dione and 4-sulfonamidophenylhydrazine hydrochloride according to Procedure G gave the title compound in 76% yield: 1H NMR (DMSO-d6): δ 2.11 (quintet, J=7.8 Hz, 2H), 3.00 (t, J=7.8 Hz, 2H), 3.06 (t, J=7.8 Hz, 2H), 6.74 (d, J=7.7 Hz, 1H), 6.97 (d, J=7.7 Hz, 1H), 7.07 (s, 1H), 7.21 (t, J=7.7 Hz, 1H), 7.25 (s, 2H), 7.47 (d, J=8.7 Hz, 2H), 7.81 (d, J=8.7 Hz, 2H), 11.12 (s, 1H), 13.03 (s, 1H); APCI−MS m/z 381 (M−1)−.

Quellen und Nachweise

ORD-Eintrag
ord-ab25a9e7185b435c9ff98418ee544d19
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06387919B1

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