Sodium Hydroxide → Tert-butyl 2-(5-bromo-2-chlorophenyl)-1H-benzimidazole-1-carboxylate

HRID 77068

Reaktionsgleichung

Reaktionsgleichung von HRID 77068
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:17])=[C:6]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[N:9]=2)[CH:7]=1.[OH-].[Na+].[O:20](C(OC(C)(C)C)=O)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=O>C1COCC1>[C:24]([O:23][C:21]([N:12]1[C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[N:9]=[C:8]1[C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[Cl:17])=[O:20])([CH3:27])([CH3:26])[CH3:25]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 433790662-(5-Bromo-2-chlorophenyl)-1H-benzo[d]imidazole

Produkt 1

HCID 66977869Tert-butyl 2-(5-bromo-2-chlorophenyl)-1H-benzimidazole-1-carboxylateAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Method 2—Step b—Into a three necked round bottomed flask equipped with a magnetic stirrer, 2-(5-bromo-2-chlorophenyl)-1H-benzimidazole (30.7 g, 99.8 mmol) was suspended in THF(1 L). 50% NaOH (72.0 g, 598 mmol) was then added. The suspension was left at r.t. for 1 h under stirring. (BOC)2O (37.0 g, 169.7 mmol) was dissolved in THF (200 mL) and added to the reaction mixture. The reaction was left under stirring overnight. The solvent was evaporated under reduced pressure. The obtained residue was diluted with water (500 mL) filtered and dried under vacuum (60° C.), to give 39.8 g of a brown solid. (98%).

Aufarbeitung

  1. customMethod 2—Step b—Into a three necked round bottomed flask equipped with a magnetic stirrer
  2. additionadded to the reaction mixture
  3. waitThe reaction was left
  4. stirringunder stirring overnight
  5. customThe solvent was evaporated under reduced pressure
  6. additionThe obtained residue was diluted with water (500 mL)
  7. filtrationfiltered
  8. customdried under vacuum (60° C.)

Quellen und Nachweise

ORD-Eintrag
ord-82df256a86b24fc29597689e2ee1f8a8
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835648B2

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