Water → Ethyl 2-(1,2,3-benzothiadiazol-7-yl)cyclopropanecarboxylate

HRID 1639846

Reaction equation

HRID 1639846 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[S:9]1[C:13]2[C:14](/[CH:18]=[CH:19]/[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[N:10]1.O>CS(C)=O>[S:9]1[C:13]2[C:14]([CH:18]3[CH2:4][CH:19]3[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[N:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 66720648ethyl(2E)-3-(1,2,3-benzothiadiazol-7-yl)acrylate

Product 1

HCID 59334567Ethyl 2-(1,2,3-benzothiadiazol-7-yl)cyclopropanecarboxylateYield 47.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a suspension of 60% sodium hydride (1.34 g, 30.7 mmol) in dimethyl sulfoxide (20 mL) was added a solution of trimethylsulfoxonium iodide (6.76 g, 30.7 mmol) in dimethyl sulfoxide (50 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added a solution of ethyl(2E)-3-(1,2,3-benzothiadiazol-7-yl)acrylate (6.00 g, 25.6 mmol) in dimethyl sulfoxide (130 mL) at 0° C., and the mixture was stirred at room temperature for 6 hr. Water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/2) to give the title compound (3.00 g, yield 47%).

Workup

  1. stirringthe mixture was stirred at room temperature for 6 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-93e41ad5e5be47a09ee6f4558adb608a
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Linked notes

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