Hydrochloric Acid → HCID 13913566, compound

HRID 330026Notes

Reaction equation

HRID 330026 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([S:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=1)[CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1.Cl>CO>[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([S:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:26][CH:27]=1)[CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15055906HCID 15055906, compound

Product 1

HCID 13913566HCID 13913566, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

694 μl of a 1N aqueous solution of sodium hydroxide were added to a solution of 61.5 mg of methyl 4-[1-(2-hydroxyphenyl)-2-(imidazol-1-yl)ethylthio]benzoate (prepared as described in Example 33) in 694 μl of methanol, and the resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was then neutralized with 694 μl of a 1N aqueous solution of hydrochloric acid, and methanol was removed by distillation under reduced pressure. The remaining solution was subjected to chromatography through a Lobar column (Lichroprep, trade mark, RP-8, size B, produced by Merck) to give 32.2 mg of the title compound as a powdery substance, melting at 186°-190° C., from the fraction eluted with 30% v/v aqueous methanol.

Workup

  1. customwas removed by distillation under reduced pressure
  2. customThe remaining solution was subjected to chromatography through a Lobar column (Lichroprep, trade mark, RP-8, size B, produced by Merck)

Sources & evidence

ORD record
ord-99da1f94b0bc46b19d9b9923686b5fe6
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

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