Hydrochloric Acid → HCID 178418633, compound

HRID 6366Notes

Reaction equation

HRID 6366 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([O:18]C)=[O:17])[N:3]=[CH:2]1.[OH-].[Na+].[ClH:22]>CO>[ClH:22].[ClH:22].[NH:1]1[CH:5]=[C:4]([CH2:6][NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([OH:18])=[O:17])[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178418660HCID 178418660, compound

Product 1

HCID 178418633HCID 178418633, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of methyl (E)-3-[2-(4-imidazolylmethylamino)phenyl]propenoate (0.7 g) in methanol (7 ml) was added 1N sodium hydroxide aqueous solution (3 ml) and the mixture was stirred for 20 hours. After removal of methanol from the reaction mixture, water was added to the residue. The mixture was adjusted to pH 6 with acetic acid. The mixture was salted out and extracted with ethyl acetate 8 times. The extracts were combined and dried over magenessium sulfate. Removal of the solvent afforded an orange oil, which was dissolved in methanol (5 ml). To the solution was added an ethereal solution of hydrogen chloride. The resultant precipitate was collected by filtration, washed with ether twice and dried to give (E)-3-[2-(4-imidazolylmethylamino)phenyl]propenoic acid dihydrochloride (0.29 g).

Workup

  1. customAfter removal of methanol from the reaction mixture, water
  2. additionwas added to the residue
  3. extractionextracted with ethyl acetate 8 times
  4. dry with materialdried over magenessium sulfate
  5. customRemoval of the solvent
  6. customafforded an orange oil, which
  7. filtrationThe resultant precipitate was collected by filtration
  8. washwashed with ether twice
  9. customdried

Sources & evidence

ORD record
ord-9cac606d071b4395a00aaae08346ef5c
Source dataset
uspto-grants-1993_09
Patent number
US05248679

Reaction notes

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