Isobutylene → HCID 178440732, Verbindung

HRID 1263974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1263974
[CH3:1][C:2]([CH3:15])=[CH:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=O)[C:7](=[O:13])[NH:8]2.IC1C=CC=C2C=1C(=O)C(=O)N2.CC(=C)C.[CH:32]1[C:37]([NH:38][NH2:39])=[CH:36][CH:35]=[C:34]([S:40]([NH2:43])(=[O:42])=[O:41])[CH:33]=1.Cl>>[CH3:1][C:2]([CH3:15])=[CH:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[N:39][NH:38][C:37]1[CH:36]=[CH:35][C:34]([S:40]([NH2:43])(=[O:41])=[O:42])=[CH:33][CH:32]=1)[C:7](=[O:13])[NH:8]2

Komponenten

5

Edukt 4

HCID 8255IsobutyleneHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 106359514-Iodoindoline-2,3-dioneHCID 110417934-(2-methyl-propenyl)-1H-indole-2,3-dione

Produkt 1

HCID 178440732HCID 178440732, VerbindungAusbeute 51 %

Versuchsvorschrift

By methods described in Procedure L, 4-(2-methyl-propenyl)-1H-indole-2,3-dione was prepared from 4-iodo-1H-indole-2,3-dione and isobutylene in 34% yield: 1H NMR (DMSO-d6): δ 1.82 (s, 3H), 1.90 (s, 3H), 6.79 (d, J=7.9 Hz, 1H), 6.94 (d, J=7.9 Hz, 1H), 7.47 (t, J=7.9 Hz, 1H), 10.97 (s, 1H); APCI−MS m/z 200 (M−1)−. Condensation of 4-(2-methyl-propenyly1H-indole-2,3-dione and 4-sulfonamidophenylhydrazine hydrochloride according to Procedure G gave the title compound as a yellow solid (51% yield): 1H NMR (DMSO-d6): δ 1.84 (s, 3H), 2.04 (s, 3H), 6.78 (s, 1H), 6.79 (d, J=7.8 Hz, 1H), 6.96 (d, J=7.8 Hz, 1H), 7.24 (t, J=7.8 Hz, 1H), 7.24 (s, 2H), 7.48 (d, J=8.8 Hz, 2H), 7.80 (d, J=8.8 Hz, 2H), 11.11 (s, 1H), 12.91 (s, 1H); APCI−MS m/z 369 (M−1)−. Anal. Calcd for C18H18N4O3S: C, 58.36, H. 4.90; N, 15.12; S, 8.66. Found C, 58.41, H. 4.87; N, 15.18; S, 8.56.

Quellen und Nachweise

ORD-Eintrag
ord-4520952c00c94d90b83a3cd97cb2ffca
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541503B2

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