Hydrochloric Acid → HCID 178418631, compound

HRID 5233Notes

Reaction equation

[O:1]=[C:2]1[O:6][NH:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][N:20]3[C:24]4[C:25]([C:29]([O:31]C)=[O:30])=[CH:26][CH:27]=[CH:28][C:23]=4[N:22]=[C:21]3[CH2:33][CH2:34][CH3:35])=[CH:15][CH:14]=2)=[N:3]1.[OH-].[Na+].Cl>>[O:1]=[C:2]1[O:6][NH:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][N:20]3[C:24]4[C:25]([C:29]([OH:31])=[O:30])=[CH:26][CH:27]=[CH:28][C:23]=4[N:22]=[C:21]3[CH2:33][CH2:34][CH3:35])=[CH:15][CH:14]=2)=[N:3]1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 178418623HCID 178418623, compound

Product 1

HCID 178418631HCID 178418631, compoundYield 90%

Conditions

Temperature: 60 °C

Procedure

A mixture of methyl 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]-2-propylbenzimidazole-7-carboxylate (703 mg) in 0.3N-NaOH (12 ml) was stirred at 60° C. for one hour, and then adjusted to pH 3 with 0.1N-HCl. Resulting precipitates were extracted with a mixture of chloroform-ethanol (10:1; 150 ml). The solvent was evaporated under reduced pressure, and the residue was crystallized from methanol to give the title compound as colorless prisms (550 mg, 90%), m.p. 169°-171° C.

Workup

customResulting
customprecipitates
extractionwere extracted with a mixture of chloroform-ethanol (10:1; 150 ml)
customThe solvent was evaporated under reduced pressure
customthe residue was crystallized from methanol

Sources & evidence

ORD record: ord-183122e9f21147948277859f6c856c2c
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05243054

Reaction notes

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