Methanesulfonic Acid → HCID 53860911, compound

HRID 442870Notes

Reaction equation

HRID 442870 reaction equation
C(O[CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=O)C.[CH2:18]([N:20]([CH2:33][CH3:34])[S:21]([C:24]1[NH:25][C:26]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:23])=[O:22])[CH3:19].CS(O)(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:33]([N:20]([CH2:18][CH3:19])[S:21]([C:24]1[NH:25][C:26]2[C:31]([C:32]=1[CH:5]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:22])=[O:23])[CH3:34]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 274281Diphenylmethyl acetateHCID 516892Sodium BicarbonateHCID 53714353HCID 53714353, compound

Product 1

HCID 53860911HCID 53860911, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzhydryl acetate (0.77 g, 3.39 mmol) and N,N-diethylindole-2-sulfonamide (0.9 g, 3.39 mmol) in 20 ml of methylene chloride was added methanesulfonic acid (0.7 ml, 10.7 mmol), followed by stirring at room temperature for one hour. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution for neutralization followed by extraction with chloroform. The resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to give a crude product. The obtained crude product was crystallized from diisopropyl ether to give 0.99 g (yield: 67%) of the title compound.

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  3. dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto give a crude product
  6. customThe obtained crude product
  7. customwas crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-ae62ab33e27847428b61b292501bac40
Source dataset
uspto-grants-1999_04
Patent number
US05891902

Reaction notes

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