Hydrochloric Acid → HCID 44482020, compound

HRID 452720Notes

Reaction equation

HRID 452720 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]4[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=4)[C:11]=3[CH:25]=2)=[N:4][N:3]=1.[OH-].[Na+].O1CCCC1.Cl>O.CO>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]4[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:23][CH:24]=4)[C:11]=3[CH:25]=2)=[N:4][N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 44481209HCID 44481209, compound

Product 1

HCID 44482020HCID 44482020, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 4-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-1-benzofuran-3-yl]benzoate (204 mg, 0.610 mmol), 1 M aqueous sodium hydroxide solution (3 mL), tetrahydrofuran (6 mL) and methanol (6 mL) was stirred at 60° C. for 24 hr. After cooling, the reaction mixture was poured into water, and acidified with 1M hydrochloric acid. The precipitate was collected by filtration, dried, and recrystallized from ethanol to give the title compound (163 mg, yield 83%) as colorless crystals.

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitate was collected by filtration
  3. customdried
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-099ac97e9f66457a97ecb2f6a66b026d
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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