Sodium hydride → Dimethyl 4-(5-chloro-3-methylbenzo[b]thiophene-2-sulfonylamino)isophthalate

HRID 748485Notes

Reaction equation

HRID 748485 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[C:12]([O:14][CH3:15])=[O:13].[H-].[Na+].[Cl:18][C:19]1[CH:32]=[CH:31][C:22]2[S:23][C:24]([S:27](Cl)(=[O:29])=[O:28])=[C:25]([CH3:26])[C:21]=2[CH:20]=1>C1COCC1>[Cl:18][C:19]1[CH:32]=[CH:31][C:22]2[S:23][C:24]([S:27]([NH:1][C:2]3[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=3[C:12]([O:14][CH3:15])=[O:13])(=[O:28])=[O:29])=[C:25]([CH3:26])[C:21]=2[CH:20]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chlorideHCID 11095854Dimethyl 4-aminoisophthalate

Product 1

HCID 22041453Dimethyl 4-(5-chloro-3-methylbenzo[b]thiophene-2-sulfonylamino)isophthalateYield 29.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into 8 mL of THF was dissolved 115 mg of dimethyl 4-aminoisophthalate, followed by addition of 22 mg of sodium hydride (oily, 60%). After 20 minutes of stirring at room temperature, 130 mg of 5-chloro-2-chlorosulfonyl-3-methylbenzo[b]thiophene was added at the same temperature, followed by 30 minutes of stirring at room temperature. Further, 26 mg of sodium hydride (oily, 60%) was added and the whole was heated under refluxing for 6 hours. After confirmation of disappearance of the starting material, the reaction was terminated by adding saturated aqueous ammonium chloride solution at 0° C., followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) to obtain 62 mg of the title compound as light yellow amorphous.

Workup

  1. waitfollowed by 30 minutes
  2. stirringof stirring at room temperature
  3. temperaturethe whole was heated
  4. temperatureunder refluxing for 6 hours
  5. customAfter confirmation of disappearance of the starting material, the reaction was terminated
  6. additionby adding saturated aqueous ammonium chloride solution at 0° C.
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was removed by evaporation
  11. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-8e452213ad9d4732979d7782a461beab
Source dataset
uspto-grants-2008_07
Patent number
US07399781B2

Reaction notes

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