Diethyl Ether → HCID 22402908, compound

HRID 375078Notes

Reaction equation

HRID 375078 reaction equation
[H-].[Na+].[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[N:4]1.CI.[CH3:19]COCC>O1CCCC1>[CH3:19][CH:12]([C:5]1[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[S:3][N:4]=1)[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 610070HCID 610070, compound

Product 1

HCID 22402908HCID 22402908, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of sodium hydride (1.25 g, 60% in oil, 31.3 mmol) in tetrahydrofuran is added to a solution of methyl 1,2-benzisothiazole-3-acetate (6.0 g, 29.0 mmol) in tetrahydrofuran. After stirring for 30 minutes, the reaction mixture is treated with methyl iodide (2.0 mL, 32.0 mmol), stirred for one hour and quenched with ice. The aqueous mixture is neutralized with hydrochloric acid (pH5-pH6) and extracted with methylene chloride. The organic extracts are combined, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a brown oil. Chromatography of the oil using silica gel and 10% to 25% ether in hexanes solutions gives the title product as an amber oil which is identified by NMR spectral analyses.

Workup

  1. stirringstirred for one hour
  2. customquenched with ice
  3. extractionextracted with methylene chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a brown oil

Sources & evidence

ORD record
ord-b5af2eaeebc3425eb8efd292ce2c60bc
Source dataset
uspto-grants-1996_01
Patent number
US05484763

Reaction notes

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