Sodium Chloride → 2-(4-Tert-butylthiazol-2-yl)benzofuran-5-carboxylic acid

HRID 1604638Notes

Reaction equation

HRID 1604638 reaction equation
[Cl-].[Na+].[C:3]([C:7]1[N:8]=[C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][C:15]=3[CH:16]=2)[S:10][CH:11]=1)([CH3:6])([CH3:5])[CH3:4].P([O-])([O-])(O)=[O:24].[Na+].[Na+].S.[Na]>C(O)(C)(C)C.O1CCCC1.O>[C:3]([C:7]1[N:8]=[C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([C:21]([OH:24])=[O:22])=[CH:17][C:15]=3[CH:16]=2)[S:10][CH:11]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 24203Sodium Phosphate, DibasicHCID 196038064-Tert-butyl-2-(5-formylbenzofuran-2-yl)thiazoleHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 196036942-(4-Tert-butylthiazol-2-yl)benzofuran-5-carboxylic acidYield 87.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium chloride (0.47 g) was added to a mixture of 4-tert-butyl-2-(5-formylbenzofuran-2-yl)thiazole (0.41 g), sodium hydrogenphosphate 12 water (0.23 g) and 2-methyl-2-butane (0.69 ml) in a mixed solvent of water (3 ml), tetrahydrofuran (7.5 ml) and tert-butanol (12.6 ml). After 4 hours, aqueous sodium hydrogensulfide solution was added to the mixture. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in 1N-sodium hydroxide and the solution was treated with carbon powder and acidified with diluted hydrochloric acid. The resulting precipitates were collected and washed with water to give 2-(4-tert-butylthiazol-2-yl)benzofuran-5-carboxylic acid (0.38 g).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in 1N-sodium hydroxide
  6. additionthe solution was treated with carbon powder
  7. customThe resulting precipitates
  8. customwere collected
  9. washwashed with water

Sources & evidence

ORD record
ord-aaac001678ab4cbca26d8747b33292d8
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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