4-Methyl-1,3-isobenzofurandione → 4-Methyl-1,3-isobenzofurandione

HRID 849247

Reaktionsgleichung

Reaktionsgleichung von HRID 849247
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([NH2:18])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].[CH3:19][C:20]1[CH:30]=[CH:29][CH:28]=[C:22]2[C:23]([O:25][C:26](=[O:27])[C:21]=12)=[O:24]>C(O)(=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([N:18]2[C:26](=[O:25])[C:21]3[C:22](=[CH:28][CH:29]=[CH:30][C:20]=3[CH3:19])[C:23]2=[O:24])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([NH2:18])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].[CH3:19][C:20]1[CH:30]=[CH:29][CH:28]=[C:22]2[C:23]([O:25][C:26](=[O:27])[C:21]=12)=[O:24]

Komponenten

6

Edukt 2

HCID 985004-Methyl-1,3-isobenzofurandioneHCID 112887921-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine

Produkt 3

HCID 985004-Methyl-1,3-isobenzofurandioneHCID 112887921-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamineHCID 193618402-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-methylisoindoline-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-methylisoindoline-1,3-dione was prepared by the procedure of Example 8 from 1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethylamine (1.4 g, 5.0 mmol) and 3-methylphthalic anhydride (810 mg, 5.0 mmol) in acetic acid (15 mL) to afford 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethylamine (1.0 g, 3.7 mmol) and 3-methylphthalic anhydride (590 mg, 3.7 mmol). The product was obtained as a white solid (1.78 g, 85% yield); mp, 143.0-145.0° C.; 1H NMR (CDCl3) δ 1.46 (t, J=7.0 Hz, 3H, CH3), 2.67 (s, 3H, CH3), 2.83 (s, 3H, CH3), 3.79 (dd, J=4.8, 14.5 Hz, 1H, CHH), 3.85 (s, CH, CH3), 4.11 (q, J=7.0 Hz, 2H, CH2), 4.54 (dd, J=9.8, 14.5 Hz, 1H, CHH), 5.89 (dd, J=4.8, 9.9 Hz, 1H, NCH), 6.81-6.85 (m, 1H, Ar), 7.65 (d, J=7.5 Hz, 1H, Ar); 13C NMR (CDCl3) δ 14.65, 17.54, 41.49, 48.63, 54.89, 55.89, 64.44, 111.36, 112.48, 120.44, 121.17, 128.24, 129.69, 132.00, 133.69, 136.63, 138.29, 148.51, 149.55, 167.99, 168.46; Anal Calcd for C21H23NO6S: C, 60.42; H, 5.55; N, 3.36. Found: C, 60.68; 11, 5.40; N, 3.15.

Quellen und Nachweise

ORD-Eintrag
ord-71d2a60640e94d9da95ac2e1319c0398
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06011050

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