Sodium hydride → 4-(3,5-Dimethyl-benzo[b]thiophene-2-sulfonylamino)-3-methanesulfonyl-benzoic acid methyl ester

HRID 1790226Notes

Reaction equation

HRID 1790226 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[S:12]([CH3:15])(=[O:14])=[O:13].[H-].[Na+].Cl[S:19]([C:22]1[S:26][C:25]2[CH:27]=[CH:28][C:29]([CH3:31])=[CH:30][C:24]=2[C:23]=1[CH3:32])(=[O:21])=[O:20]>C1COCC1>[CH3:31][C:29]1[CH:28]=[CH:27][C:25]2[S:26][C:22]([S:19]([NH:1][C:2]3[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=3[S:12]([CH3:15])(=[O:14])=[O:13])(=[O:21])=[O:20])=[C:23]([CH3:32])[C:24]=2[CH:30]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 220414653,5-Dimethyl-1-benzothiophene-2-sulfonyl chlorideHCID 22041468methyl 4-Amino-3-methylsulfonylbenzoate

Product 1

HCID 220414554-(3,5-Dimethyl-benzo[b]thiophene-2-sulfonylamino)-3-methanesulfonyl-benzoic acid methyl esterYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into 8.0 mL of THF was dissolved 183 mg of methyl 4-amino-3-methanesulfonylbenzoate, followed by addition of 96 mg of sodium hydride (oily, 60%) at 0° C. After 20 minutes of stirring at the same temperature, 250 mg of 2-chlorosulfonyl-5-methyl-3-methylbenzo[b]thiophene was added at 0° C., followed by 6 hours of stirring at room temperature. After confirmation of disappearance of the starting material, the reaction was terminated by adding 1 mol/L hydrochloric acid at 0° C., followed by extraction with chloroform. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation and then the residue was purified by silica gel column chromatography (ethyl acetate/hexane=3/1 to 1/1) to obtain 181 mg of the title compound as colorless powder.

Workup

  1. additionwas added at 0° C.
  2. customAfter confirmation of disappearance of the starting material, the reaction was terminated
  3. additionby adding 1 mol/L hydrochloric acid at 0° C.
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed by evaporation
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=3/1 to 1/1)

Sources & evidence

ORD record
ord-b427e01b17ac4285894a0f804cc42901
Source dataset
uspto-grants-2006_07
Patent number
US07071220B2

Reaction notes

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