Ethylene Glycol → 4-(benzyloxy)-2-methyl-1H-benzo[d]imidazole-6-carboxylic acid

HRID 2239289Notes

Reaction equation

HRID 2239289 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=C(C#N)[CH:9]=[C:10]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]=2[N:3]=1.[OH-:21].[K+].Cl.[CH2:24]([OH:27])[CH2:25]O>>[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[C:25]([C:24]([OH:27])=[O:21])[CH:9]=[C:10]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]=2[N:3]=1

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 685763664-(benzyloxy)-2-methyl-1H-benzo[d]imidazole-6-carbonitrile

Product 1

HCID 685745314-(benzyloxy)-2-methyl-1H-benzo[d]imidazole-6-carboxylic acidYield 93%

Procedure

A solution of 2-methyl-4-[(phenylmethyl)oxy]-1H-benzimidazole-6-carbonitrile (3.82 g, 14.5 mmol, STEP 3) and potassium hydroxide (85%, 10.2 g, 15.4 mmol) in ethylene glycol (50 mL) was heated to 170° C. for 20 minutes in the microwave synthesizer (Biotage, Emrys Optimizer). After cooling to room temperature, the mixture was acidified with 2M hydrochloric acid aqueous solution (pH=3). The precipitated solid was collected by filtration to afford the title compound as a white solid (3.83 g, 93%).

Workup

  1. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-dbfc30294c3d4fac93e67a92d26653cf
Source dataset
uspto-grants-2010_05
Patent number
US07723321B2

Reaction notes

Loading…