Sodium hydride → HCID 86747952, compound

HRID 1110008Notes

Reaction equation

HRID 1110008 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6]O.[H-].[Na+].[H][H].O1C2C=CC=CC=2N=C1SCCCCC[N:27]1[C:31](=[O:32])[C:30]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]2[C:28]1=[O:37]>CN(C)C=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][S:1][CH2:5][CH2:4][CH2:3][CH2:2][CH2:6][C:36]1[CH:35]=[CH:34][CH:33]=[C:30]2[C:31]([NH:27][C:28](=[O:37])[C:29]=12)=[O:32]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 694672-ThiophenemethanolHCID 19018706HCID 19018706, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86747952HCID 86747952, compoundYield 159.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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%.

Workup

  1. stirringThe resulting mixture was stirred for 3 hours with ice cooling and for 60 hours at room temperature
  2. customto give rise
  3. customto a reaction
  4. customAfter the completion of the reaction
  5. extractionExtraction with benzene
  6. washThe benzene layer was washed with water
  7. dry with materiala saturated aqueous sodium chloride solution in this order and dried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation
  9. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e2f9a63ddf9549a7b8445218f38e5608
Source dataset
uspto-grants-1994_06
Patent number
US05324728

Reaction notes

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