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

HRID 487693Notes

Reaction equation

HRID 487693 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]Cl)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:21]([OH:30])(=[O:29])[C:22]1[C:23](=[CH:25][CH:26]=[CH:27][CH:28]=1)[SH:24].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[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][S:24][C:23]4[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=4[C:21]([OH:30])=[O:29])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 54432-Mercaptobenzoic AcidHCID 11430Potassium CarbonateHCID 19603727HCID 19603727, compound

Product 1

HCID 190927324-Tert-butyl-2-[5-(2-carboxyphenylthiomethyl)benzofuran-2-yl]thiazoleYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-tert-butyl-2-(5-chloromethylbenzofuran-2-yl)thiazole (0.68 g) and thiosalicylic acid (0.72 g) in N,N-dimethylformamide (5 ml), potassium carbonate (0.78 g) was added dropwise at 100° C. After being stirred for one hour, the reaction mixture was cooled, poured into a mixture of ice and diluted aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate solution to remove thiosalicylic acid, dried over magnesium sulfate and concentrated under reduced pressure. The residue was crystallized with ethyl acetate and filtered to give 4-tert-butyl-2-[5-(2-carboxyphenylthiomethyl)benzofuran-2-yl]thiazole (0.49 g).

Workup

  1. temperaturethe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with aqueous sodium hydrogen carbonate solution
  4. customto remove thiosalicylic acid
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized with ethyl acetate
  8. filtrationfiltered

Sources & evidence

ORD record
ord-118176139a054907a3b9490a2e21ca11
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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