Sodium hydride → HCID 86747952, compound

Participants

Reaction Steps

2 g (17.5 mM) of 2-thiophenemethanol was dissolved in 15 ml of dimethylformamide. Thereto was added 800 mg (20 mM) of 60% sodium hydride in a nitrogen stream with ice cooling, and the mixture was stirred. When hydrogen generation was over, thereto was dropwise added a solution of 6.5 g of N-{5-(2-benzoxazolylthio)pentyl}phthalimide in 30 ml of DMF. The resulting mixture was stirred for 3 hours with ice cooling and for 60 hours at room temperature to give rise to a reaction. After the completion of the reaction, the reaction mixture was placed in ice water. Extraction with benzene was conducted. The benzene layer was washed with water and a saturated aqueous sodium chloride solution in this order and dried over anhydrous sodium sulfate. The solvent was removed by distillation. The residue was purified by silica gel chromatography to obtain 4.84 g of N-{5-(2-thienylmethylthio)pentylphthalimide at a yield of 80%.

Provenance & Evidence