Hydrochloric Acid → 4-Tert-butyl-2-[5-(2-carboxyphenylmethoxy)benzofuran-2-yl]thiazole

HRID 487684Notes

Reaction equation

HRID 487684 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]([O:29]C)=[O:28])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO.O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]([OH:29])=[O:28])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 190927604-Tert-butyl-2-[5-(2-methoxycarbonylphenylmethoxy)benzofuran-2-yl]thiazole

Product 1

HCID 190927584-Tert-butyl-2-[5-(2-carboxyphenylmethoxy)benzofuran-2-yl]thiazoleYield 99.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-tert-butyl-2-[5-(2-methoxycarbonylphenylmethoxy)benzofuran-2-yl]thiazole (0.28 g) and 4N aqueous sodium hydroxide (1.0 ml) in methanol (5 ml) was stirred under reflux 5.5 hours. After being cooled, the resulting solution was concentrated under reduced pressure to give a residue. The residue was dissolved in water and adjusted to pH 4 with diluted aqueous hydrochloric acid to give crystals. The crystals were filtered and washed with water to give 4-tert-butyl-2-[5-(2-carboxyphenylmethoxy)benzofuran-2-yl]thiazole (0.27 g).

Workup

  1. temperatureunder reflux 5.5 hours
  2. temperatureAfter being cooled
  3. concentrationthe resulting solution was concentrated under reduced pressure
  4. customto give a residue
  5. customto give crystals
  6. filtrationThe crystals were filtered
  7. washwashed with water

Sources & evidence

ORD record
ord-18c47e5cef6e4ad7b27097a6505279fd
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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