Sodium Hydroxide → HCID 19603666, compound

HRID 1604652Notes

Reaction equation

HRID 1604652 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][C:20]4[S:21][CH:22]=[C:23]([C:25]([O:27]CC)=[O:26])[N:24]=4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O.CO>[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][C:20]4[S:21][CH:22]=[C:23]([C:25]([OH:27])=[O:26])[N:24]=4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19603722HCID 19603722, compound

Product 1

HCID 19603666HCID 19603666, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-tert-butyl-2-{5-{[4-(ethoxycarbonyl)-thiazol-2-yl]methyl}benzofuran-2-yl}thiazole (0.79 g) and sodium hydroxide (0.17 g) in a mixture of water (2 ml) and methanol (6 ml) was stirred under reflux for 3 hours. After being cooled, the resulting solution was concentrated under reduced pressure. The residue was dissolved in water and neutralized with diluted hydrochloric acid. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in reduced pressure. The residue was washed with a small amount of ethyl acetate to give 4-tert-butyl-2-{5-{[4-carboxythiazol-2-yl]methyl}benzofuran-2-yl}thiazole (0.69 g).

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter being cooled
  3. concentrationthe resulting solution was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in water and neutralized with diluted hydrochloric acid
  5. extractionThe resulting mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in reduced pressure
  9. washThe residue was washed with a small amount of ethyl acetate

Sources & evidence

ORD record
ord-d98397431c4347fa8e04c81d74419a5b
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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