Benzenesulfonyl chloride → HCID 16222448, compound

HRID 1098653Notes

Reaction equation

HRID 1098653 reaction equation
[H-].[K+].[CH3:3][N:4]([CH3:18])[CH:5]1[CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[CH2:7][CH2:6]1.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCCC1>[C:19]1([S:25]([N:9]2[C:8]3[CH2:7][CH2:6][CH:5]([N:4]([CH3:18])[CH3:3])[CH2:17][C:16]=3[C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=3)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 36082CyclindoleHCID 82127Potassium hydride

Product 1

HCID 16222448HCID 16222448, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

Taken potassium hydride 153.80 mg, 1.15 mM (30% suspension in mineral oil) in tetrahydrofuran (15 ml) and stirred at 25° C. for 10 mt. The reaction mixture was cooled to 10-15° C. Dimethyl-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)amine (190 mg, 0.88 mM), dissolved in 5 ml of THF, was added slowly under stirring maintaining mass temperature below 25° C. The reaction mass was further stirred for 1 hour at 25° C. Then added a solution of Benzene sulphonyl chloride (235 mg, 1.33 mM, dissolved in 5 ml of THF) drop wise over a period of 15 mts. The reaction mass was stirred, while monitoring the progress of the reaction by TLC, for 2 hours at 25° C. After the completion of reaction, the mixture was diluted with 75 mL of ice water and extracted with ethyl acetate; Organic layer was washed with brine solution. The ethyl acetate extract was dried over anhydrous sodium sulfate; filtered and solvent was removed under reduced pressure to obtain the exude product. The residual mass was purified by flash chromatography (silica gel, EtoAc/n-Hexane, 9/1) to get the title compound, which was characterized by IR, NMR and mass spectral analyses.

Workup

  1. temperatureThe reaction mixture was cooled to 10-15° C
  2. additionwas added slowly
  3. stirringunder stirring
  4. temperaturemaintaining mass temperature below 25° C
  5. stirringThe reaction mass was further stirred for 1 hour at 25° C
  6. stirringThe reaction mass was stirred
  7. customthe progress of the reaction by TLC
  8. customAfter the completion of reaction
  9. extractionextracted with ethyl acetate
  10. washOrganic layer was washed with brine solution
  11. extractionThe ethyl acetate extract
  12. dry with materialwas dried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. customsolvent was removed under reduced pressure
  15. customto obtain the exude product
  16. customThe residual mass was purified by flash chromatography (silica gel, EtoAc/n-Hexane, 9/1)

Sources & evidence

ORD record
ord-9e0e15693ead4688aefc62d8c92ce0dd
Source dataset
uspto-grants-2012_03
Patent number
US08143303B2

Reaction notes

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