Hydrochloric Acid → 4-Tert-butyl-2-[5-{2-(2-carboxyphenyl)ethyl}benzofuran-2-yl]thiazole

HRID 487697Notes

Reaction equation

HRID 487697 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]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]([O:29]CC)=[O:28])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl>CO.[OH-].[Na+]>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 190928114-Tert-butyl-2-[5-{2-(2-ethoxycarbonylphenyl)ethyl}benzofuran-2-yl]thiazole

Product 1

HCID 190927554-Tert-butyl-2-[5-{2-(2-carboxyphenyl)ethyl}benzofuran-2-yl]thiazoleYield 54.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 4-tert-butyl-2-[5-{2-(2-ethoxycarbonylphenyl)ethyl}benzofuran-2-yl]thiazole (170 mg) in methanol (5 ml), 1N aqueous sodium hydroxide (1.58 ml) was added. The resulting mixture was heated under reflux for 9 hours. After being cooled, 1N hydrochloric acid was added. The resulting precipitates were collected by filtration, and washed by water to give 4-tert-butyl-2-[5-{2-(2-carboxyphenyl)ethyl}benzofuran-2-yl]thiazole (86.3 mg).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 9 hours
  3. temperatureAfter being cooled
  4. customThe resulting precipitates
  5. filtrationwere collected by filtration
  6. washwashed by water

Sources & evidence

ORD record
ord-c64dff76e3244c439181ab9edd8f8375
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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