Acetic Acid → HCID 178496989, Verbindung

HRID 1898349Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1898349
[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.C(O)(=O)C>C1C=CC=CC=1.[Fe]>[NH2:24][C:15]1[C:13]2[NH:14][C:10]([NH:9][C:3]3[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[N:11][C:12]=2[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[C:16]=1[OH:23]

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 178496990HCID 178496990, Verbindung

Produkt 1

HCID 178496989HCID 178496989, VerbindungAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-[(2,6-dichlorophenyl)amino]-6-hydroxy-7-nitro-1H-benzimidazole-5-carboxylate (Step-3 of Intermediate-55, 0.500 g) in benzene (2.0 mL) were added iron powder (0.500 g) and acetic acid (2.0 mL). The reaction mass was refluxed for 3 h. Decant the reaction mass removed the solvent under vacuum. The obtained solid mass was washed with water. The reaction mass was extracted with MeOH:DCM (5%). The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 0.440 g of the desired product. 1HNMR (DMSO-d6): δ 3.87 (s, 3H), 4.45 (s, 2H), 7.28-7.47 (m, 1H), 7.53-7.59 (m, 3H), 11.00 (s, 2H).

Aufarbeitung

  1. temperatureThe reaction mass was refluxed for 3 h
  2. customDecant the reaction mass
  3. customremoved the solvent under vacuum
  4. washThe obtained solid mass was washed with water
  5. extractionThe reaction mass was extracted with MeOH
  6. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a74f317fc0c64c2fad1e1851936f9b56
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08519149B2

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