Acetic Acid → HCID 178496987, Verbindung

HRID 1898343Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1898343
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:14][C:13]2[C:15]([N+:24]([O-])=O)=[C:16]([OH:23])[C:17]([C:19]([O:21][CH3:22])=[O:20])=[CH:18][C:12]=2[N:11]=1.[In].[C:28](O)(=O)[CH3:29].C(OC)(OC)(OC)C>C1C=CC=CC=1.C(Cl)Cl.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:14][C:13]2[C:15]3[N:24]=[C:28]([CH3:29])[O:23][C:16]=3[C:17]([C:19]([O:21][CH3:22])=[O:20])=[CH:18][C:12]=2[N:11]=1

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 15050Trimethyl orthoacetateHCID 5359967IndiumHCID 178496990HCID 178496990, Verbindung

Produkt 1

HCID 178496987HCID 178496987, VerbindungAusbeute 51,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 241BenzeneLösungsmittelHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-[(2,6-dichlorophenyl)amino]-6-hydroxy-7-nitro-1H-benzimidazole-5-carboxylate (0.150 g, 0.370 mmol) in benzene (5 mL), indium (0.172 g, 1.51 mmol), acetic acid (0.468 g, 7.54 mmol) and trimethyl orthoacetate (0.480 g, 2.96 mmol) were added under N2 atmosphere. The reaction mass was refluxed for 3-4 h. A mixture of MeOH:DCM (15%) was added to the reaction mixture. The reaction mass was filtered. The organic layer was concentrated. The obtained product was further purified by column chromatography on neutral alumina eluting with 1.5-2.0% MeOH: DCM to afford 0.075 g of the desired product. 1HNMR (DMSO-d6): δ 2.63 (s, 3H), 3.88 (s, 3H), 7.40 (m, 1H), 7.61-7.69 (m, 3H), 9.56 (s, 1H), 11.56 (s, 1H); MS [M+H]+: 391.33.

Aufarbeitung

  1. temperatureThe reaction mass was refluxed for 3-4 h
  2. filtrationThe reaction mass was filtered
  3. concentrationThe organic layer was concentrated
  4. customThe obtained product was further purified by column chromatography on neutral alumina eluting with 1.5-2.0% MeOH

Quellen und Nachweise

ORD-Eintrag
ord-bd43159d89d74f87a4fd63d13a5cdf5a
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08519149B2

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