Sodium Hydroxide → 2-(2,6-dichlorophenyl)-1-methyl-1H-benzoimidazole-5-carboxylic acid

HRID 1514921Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:23]=[CH:22][C:9]2[N:10]([CH3:21])[C:11]([C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:20])=[N:12][C:8]=2[CH:7]=1)=[O:5])C.[OH-].[Na+]>CCO>[Cl:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([Cl:19])[C:13]=1[C:11]1[N:10]([CH3:21])[C:9]2[CH:22]=[CH:23][C:6]([C:4]([OH:5])=[O:3])=[CH:7][C:8]=2[N:12]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 2-(2,6-dichlorophenyl)-1-methyl-1H-benzoimidazole-5-carboxylic acid ethyl ester (400 mg) in EtOH (8 mL) was added 1.0 N NaOH (2.0 mL) and the mixture was stirred at 60° C. for 90 min. The ethanol was removed under reduced pressure and water (10 mL) was added. Any insoluble material was filtered and 2.0N HCl (2.0 mL) was added to the filtrate. The resulting precipitate was filtered, washed with water and dried under reduced pressure to give 2-(2,6-dichlorophenyl)-1-methyl-1H-benzoimidazole-5-carboxylic acid as a white solid, mp>250° C.; MS (m/z) 321 (M+1).

Workup

customThe ethanol was removed under reduced pressure and water (10 mL)
additionwas added
filtrationAny insoluble material was filtered
addition2.0N HCl (2.0 mL) was added to the filtrate
filtrationThe resulting precipitate was filtered
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-7079db5bfa2b494cba51ccec150ca648
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222248B2

Reaction notes

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