Water → 2-(1H-Indol-5-yl)-N-methylethane-1-sulfonamide

HRID 1028418Notes

Reaction equation

HRID 1028418 reaction equation
[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14]C(=O)C)=[C:10]([C:18]#[C:19][Si](C)(C)C)[CH:9]=1)(=[O:5])=[O:4].CC(C)([O-])C.[K+].O.CCCCCCC>CN1CCCC1=O>[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:11](=[CH:12][CH:13]=1)[NH:14][CH:19]=[CH:18]2)(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8900HeptaneHCID 23665647Potassium tert-butoxideHCID 66973773HCID 66973773, compound

Product 1

HCID 134757652-(1H-Indol-5-yl)-N-methylethane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
82.5 °C

Procedure

N-[4-(2-methylsulfamoyl-ethyl)-2-trimethylsilanylethynyl-phenyl]-acetamide (100 gm) was dissolved in N-methylpyrrolidone (900 ml) at 25° C. under inert atmosphere. Potassium tert-butoxide (49 g) was added and heated to 80-85° C. for 120-150 minutes. The reaction mass was cooled gradually to 25° C., water (3000 ml) was added and stirred for 30 minutes. The solution was extracted with ethyl acetate (2000 ml). The organic layer was dried over sodium sulfate and vacuum distilled to obtain a residue. The residue was treated with heptane (300 ml) to obtain a solid. The solid was filtered, washed with heptane and dried at 50-55° C. under vacuum to obtain title compound. (Yield: 74 g, HPLC Purity: 98%)

Workup

  1. temperatureThe reaction mass was cooled gradually to 25° C.
  2. extractionThe solution was extracted with ethyl acetate (2000 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate and vacuum
  4. distillationdistilled
  5. customto obtain a residue
  6. customto obtain a solid
  7. filtrationThe solid was filtered
  8. washwashed with heptane
  9. customdried at 50-55° C. under vacuum

Sources & evidence

ORD record
ord-2ee46eaf334f4abbaa1324e3273770c0
Source dataset
uspto-grants-2014_05
Patent number
US08735589B2

Reaction notes

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