Methyl iodide → HCID 53993041, compound

HRID 442889Notes

Reaction equation

HRID 442889 reaction equation
[C:1]1([CH:7]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[NH:8][S:9]([C:12]2[N:13]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].I[CH3:39].[Cl-].[NH4+]>CN(C)C=O.O>[C:30]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]([CH3:39])[S:9]([C:12]2[N:13]([S:21]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)(=[O:23])=[O:22])[C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:11])=[O:10])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 54205160HCID 54205160, compound

Product 1

HCID 53993041HCID 53993041, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-diphenylmethyl-1-benzenesulfonylindole-2-sulfonamide (12.40 g, 24.67 mmol) in 120 ml of N,N-dimethylformamide was portionwise added sodium hydride (60% in oil, 1.18 g, 29.61 mmol) with stirring at 0° C., and iodomethane (1.85 ml, 29.61 mmol) was added thereto. The resulting solution was heated to 50° C. and stirred for 3 hours, followed by stirring at 70° C. for 3.5 hours. The reaction solution was neutralized with a saturated aqueous solution of ammonium chloride, and water was added thereto followed by extraction with chloroform. The resulting organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to give 18.1 g of a crude product. The obtained crude product was washed with ethanol under heating to give 11.0 g (yield: 86%) of the title compound.

Workup

  1. temperatureThe resulting solution was heated to 50° C.
  2. stirringstirred for 3 hours
  3. stirringby stirring at 70° C. for 3.5 hours
  4. additionwas added
  5. extractionthereto followed by extraction with chloroform
  6. washThe resulting organic layer was washed with water
  7. dry with materiala saturated aqueous solution of sodium chloride and dried over magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customto give 18.1 g of a crude product
  10. customThe obtained crude product
  11. washwas washed with ethanol
  12. temperatureunder heating

Sources & evidence

ORD record
ord-76a6aea1c6e646bd9cec59cfb933abdc
Source dataset
uspto-grants-1999_04
Patent number
US05891902

Reaction notes

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