Hydrochloric Acid → 1-[3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]-phenyl]propyl]-2-imidazolecarboxylic acid

HRID 322386Notes

Reaction equation

HRID 322386 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]2[O:10][CH:11]=[C:12]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][N:25]4[CH:29]=[CH:28][N:27]=[C:26]4[C:30]([O:32]CC)=[O:31])=[CH:18][CH:17]=3)[N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O1CCCC1.Cl>O>[C:1]1(/[CH:7]=[CH:8]/[C:9]2[O:10][CH:11]=[C:12]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][N:25]4[CH:29]=[CH:28][N:27]=[C:26]4[C:30]([OH:32])=[O:31])=[CH:18][CH:17]=3)[N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22009644ethyl 1-[3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl]-2-imidazolecarboxylate

Product 1

HCID 220098621-[3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]-phenyl]propyl]-2-imidazolecarboxylic acidYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 1-[3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl]-2-imidazolecarboxylate (300 mg), 1N aqueous sodium hydroxide (1.32 ml) and tetrahydrofuran (3 ml) was stirred for 2 hours at room temperature. To the reaction mixture were added 1N hydrochloric acid (1.32 ml) and then water. The resulting crystalline precipitate was collected by filtration and washed with ether. Recrystallization from tetrahydrofuran gave 1-[3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]-phenyl]propyl]-2-imidazolecarboxylic acid (176 mg, 63%) as colorless prisms, mp 116° C. (decomp.).

Workup

  1. filtrationThe resulting crystalline precipitate was collected by filtration
  2. washwashed with ether
  3. customRecrystallization from tetrahydrofuran

Sources & evidence

ORD record
ord-b75e983a509b4216bb3930de880c21e5
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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