Hydrochloric Acid → 4-(5-Phenoxybenzimidazole-2-yl)-3,5-dimethylpyrrole-2-carboxylic acid

HRID 553255Notes

Reaction equation

C([O:3][C:4]([C:6]1[NH:7][C:8]([CH3:28])=[C:9]([C:12]2[NH:13][C:14]3[CH:20]=[C:19]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:18]=[CH:17][C:15]=3[N:16]=2)[C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+].Cl>C(O)C.O1CCCC1>[O:21]([C:19]1[CH:18]=[CH:17][C:15]2[N:16]=[C:12]([C:9]3[C:10]([CH3:11])=[C:6]([C:4]([OH:5])=[O:3])[NH:7][C:8]=3[CH3:28])[NH:13][C:14]=2[CH:20]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The 4-(5-phenoxybenzimidazole-2-yl)-3,5-dimethylpyrrole-2-carboxylic acid ethyl ester (1.88 g, 5.0 mmol) obtained in Example 68 was dissolved in ethanol (10 ml) and tetrahydrofuran (5 ml). To this solution was added a 4 N sodium hydroxide aqueous solution (6 ml, 24 mmol), and the mixture was stirred at 80° C. for 6 hours. The reaction mixture was cooled to 0° C., and neutralized with a 1 N hydrochloric acid solution. The precipitate was collected by filtration, and washed with water and dried at reduced pressure to afford 4-(5-phenoxybenzimidazole-2-yl)-3,5-dimethylpyrrole-2-carboxylic acid (1.70 g, 98%) as a light yellow solid.

Workup

temperatureThe reaction mixture was cooled to 0° C.
filtrationThe precipitate was collected by filtration
washwashed with water
customdried at reduced pressure

Sources & evidence

ORD record: ord-ed5f82159eff40c0b3930b0d71c39113
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951956B2

Reaction notes

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