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

HRID 1028416Notes

Reaction equation

HRID 1028416 reaction equation
C([C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][S:11](=[O:15])(=[O:14])[NH:12][CH3:13])[CH:6]=[CH:5][C:4]=1[NH:16][C:17](=O)[CH3:18])#C.CC(C)([O-])C.[K+].O.CCCCCCC>CN1CCCC1=O>[CH3:13][NH:12][S:11]([CH2:10][CH2:9][C:7]1[CH:6]=[C:5]2[C:4](=[CH:3][CH:8]=1)[NH:16][CH:17]=[CH:18]2)(=[O:14])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8900HeptaneHCID 23665647Potassium tert-butoxideHCID 53348247HCID 53348247, 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-[2-ethynyl-4-(2-methylsulfamoyl-ethyl)-phenyl]-acetamide (100 g) was dissolved in N-methylpyrrolidone (900 ml) at 25° C. Potassium tert-butoxide (60 g) was added and the reaction mass was 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 distilled under vacuum to obtain a residue. The residue was treated with heptane (300 ml) to obtain a solid which was filtered, washed with heptane and dried at 50-55° C. under vacuum to obtain the title compound. (Yield: 84 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
  4. distillationdistilled under vacuum
  5. customto obtain a residue
  6. customto obtain a solid which
  7. filtrationwas filtered
  8. washwashed with heptane
  9. customdried at 50-55° C. under vacuum

Sources & evidence

ORD record
ord-41f7f9c1a4ad4f1886832cb473006193
Source dataset
uspto-grants-2014_05
Patent number
US08735589B2

Reaction notes

Loading…