Sodium Hydroxide → HCID 70456143, compound

HRID 1249546Notes

Reaction equation

HRID 1249546 reaction equation
[ClH:1].[N:2]1([CH2:7][CH2:8][NH:9][C:10]2[CH:20]=[CH:19][C:13]([C:14]([O:16]CC)=[O:15])=[CH:12][CH:11]=2)[CH:6]=[CH:5][N:4]=[CH:3]1.[OH-].[Na+]>CO.O>[ClH:1].[N:2]1([CH2:7][CH2:8][NH:9][C:10]2[CH:20]=[CH:19][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=2)[CH:6]=[CH:5][N:4]=[CH:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20223558HCID 20223558, compound

Product 1

HCID 70456143HCID 70456143, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Then, a solution of 1.0 g of ethyl p-[β-(1-imidazolyl)ethylamino]benzoate hydrochloride and 1.0 g of sodium hydroxide in 30 ml of methanol-water (1:2 by volume) was stirred for 2.5 hours at room temperature. After concentration under reduced pressure, the residue was acidified with 6N hydrochloric acid to pH 1, and then concentrated under reduced pressure. To the residue was added 20 ml of tert-butanol and evaporated under reduced pressure to remove the excess of hydrochloric acid completely. The residual solid was dissolved in ethanol, the insoluble salts were filtered off, and then the filtrate was evaporated under reduced pressure. The residual solid was recrystallized from ethanol-diethyl ether to give 0.65 g of p-[β-(1-imidazolyl)ethylamino]benzoic acid hydrochloride as colorless needles. M.P.: 222° to 224° C. (dec.).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue was added 20 ml of tert-butanol
  4. customevaporated under reduced pressure
  5. customto remove the excess of hydrochloric acid completely
  6. dissolutionThe residual solid was dissolved in ethanol
  7. filtrationthe insoluble salts were filtered off
  8. customthe filtrate was evaporated under reduced pressure
  9. customThe residual solid was recrystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-867b426c19684123bf96e4a37c19c882
Source dataset
uspto-grants-1986_12
Patent number
US04632934

Reaction notes

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