Hydrochloric Acid → HCID 23061858, compound

HRID 350712Notes

Reaction equation

HRID 350712 reaction equation
[N:1]1([C:10]2[O:11][C:12]([CH2:25][CH2:26][C:27]([O:29]C)=[O:28])=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[N:14]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[N:1]1([C:10]2[O:11][C:12]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[C:13]([C:15]3[CH:16]=[CH:17][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=3)[N:14]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 23061767HCID 23061767, compound

Product 1

HCID 23061858HCID 23061858, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 3-{2-(1H-benzimidazol-1-yl)-4-[4-(trifluoromethyl)phenyl]-5-oxazolyl}propionate (1.00 g), 1N aqueous sodium hydroxide solution (10 mL), tetrahydrofuran (10 mL) and ethanol (10 mL) was stirred at room temperature for 1 hr. The reaction mixture was poured into dilute hydrochloric acid, and the precipitated crystals were collected by filtration, washed with water, dried and recrystallized from tetrahydrofuran-ethanol to give 3-{2-(1H-benzimidazol-1-yl)-4-[4-(trifluoromethyl)phenyl]-5-oxazolyl}propionic acid (1.00 g, yield 83%) as pale-yellow prism crystals. melting point: 224–226° C.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. washwashed with water
  3. customdried
  4. customrecrystallized from tetrahydrofuran-ethanol

Sources & evidence

ORD record
ord-bc0d964c8e394d57be091e7525c65cc5
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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