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

HRID 555285Notes

Reaction equation

HRID 555285 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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)

Workup

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

Sources & evidence

ORD record
ord-670233ff91fb4bdcb0453d61c2c8be73
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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