Methanol → 1-(2-cyanoethyl)-1H-benzoimidazole-5-carboxylic acid

HRID 555285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 555285
C[O:2][C:3]([C:5]1[CH:17]=[CH:16][C:8]2[N:9]([CH2:12][CH2:13][C:14]#[N:15])[CH:10]=[N:11][C:7]=2[CH:6]=1)=[O:4].[Li+].[OH-].CO>C1COCC1.O>[C:14]([CH2:13][CH2:12][N:9]1[C:8]2[CH:16]=[CH:17][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[N:11]=[CH:10]1)#[N:15]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 669871661-(2-cyanoethyl)-1H-benzimidazole-5-carboxylic acid methyl ester

Produkt 1

HCID 669873251-(2-cyanoethyl)-1H-benzoimidazole-5-carboxylic acidAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-(2-cyanoethyl)-1H-benzimidazole-5-carboxylic acid methyl ester (4.0 g, 17.4 mmol) in THF (30 mL) was added LiOH (1.67 g, 69.79 mmol) in water (8 mL) followed by MeOH (2 mL). Stirring continued at the ambient temperature for 1 h. It was then concentrated and acidified with 2N HCl. The solids formed were filtered and dried which afforded 1-(2-cyanoethyl)-1H-benzoimidazole-5-carboxylic acid (3.5 g, 95%). 1H NMR (300 MHz, DMSO-d6) δ 3.1 (t, 2H), 4.6 (t, 2H), 7.8 (d, 1H), 7.9 (dd, 1H), 8.25 (d, 1H), 8.42 (s, 1H)

Aufarbeitung

  1. concentrationIt was then concentrated
  2. customThe solids formed
  3. filtrationwere filtered
  4. customdried which

Quellen und Nachweise

ORD-Eintrag
ord-670233ff91fb4bdcb0453d61c2c8be73
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053431B2

Notizen zur Reaktion

Wird geladen…