Methanesulfonic Acid → N-Isopropyl-3-(diphenylmethyl)indole-2-sulfonamide

HRID 442873Notes

Reaction equation

HRID 442873 reaction equation
[CH:1](O)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15]([NH:18][S:19]([C:22]1[NH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:21])=[O:20])([CH3:17])[CH3:16].CS(O)(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:15]([NH:18][S:19]([C:22]1[NH:23][C:24]2[C:29]([C:30]=1[CH:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:21])=[O:20])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 7037BenzhydrolHCID 516892Sodium BicarbonateHCID 54122335N-isopropylindole-2-sulfonamide

Product 1

HCID 54301966N-Isopropyl-3-(diphenylmethyl)indole-2-sulfonamideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzhydrol (0.58 g, 3.15 mmol) and N-isopropylindole-2-sulfonamide (0.7 g, 3.12 mmol) in 15 ml of methylene chloride was added a solution of methanesulfonic acid (0.2 ml, 3.12 mmol) in 4 ml of methylene chloride, followed by stirring at room temperature for 2.5 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution for neutralization and the solvent was distilled off under reduced pressure, followed by extraction with ethyl acetate. The resulting organic layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to give 1.4 g of a crude product. The obtained crude product was washed with ethanol to give 1.07 g (yield: 85%) of the title compound.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe resulting organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto give 1.4 g of a crude product
  7. customThe obtained crude product
  8. washwas washed with ethanol

Sources & evidence

ORD record
ord-29f1ba2f60a248d1becc66efd0733be1
Source dataset
uspto-grants-1999_04
Patent number
US05891902

Reaction notes

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