Water → 1-(4-Methylbenzene-1-sulfonyl)-1H-indole-5-carbonitrile

HRID 1440205Notes

Reaction equation

HRID 1440205 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2)#[N:4].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.O>CCCCCC.O1CCCC1>[C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)(=[O:22])=[O:21])[CH:9]=[CH:8]2)#[N:4]

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 27513Indole-5-carbonitrile

Product 1

HCID 224925731-(4-Methylbenzene-1-sulfonyl)-1H-indole-5-carbonitrileYield 72.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

Sodium hydride (8.4 g, 210 mmol) was washed twice with hexane and then suspended in tetrahydrofuran (500ml). 5-Cyanoindole (20g, 140 mmol) in tetrahydrofuran (200 ml) was added dropwise. The resulting mixture was stirred at ambient temperature for 1 hour and then p-toluenesulfonyl chloride (26.7 g, 140 mmol) in tetrahydrofuran (200 ml) was added. The reaction was stirred 3 hours more followed by addition of water. The phases were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic phase was washed with brine, dried over calcium sulfate and concentrated. The residue was recrystallized from ether to afford 29.97 g, 72% of title product; m.p. 129°-131° C.; NMR 8.04 (d, J=8.5 Hz, 1H), 7.85 (d, J=1 Hz, 1H), 7.75 (d, J=9 Hz, 2H), 7.67 (d, J=3.5 Hz, 1H), 7.23 (m, 2H), 6.68 (d, J=3.5 Hz, 1H), 2.34 (s, 3H). IR(CHCl3 solution) 2225, 1597, 1453, 1380, 1289, 1266, 1169, 1138, 1123, 1089 (shoulder), 990. FAB HRMS calcd for C16H13N2O2S(MH+): 297.0669. Observed m/e: 297.0685.

Workup

  1. stirringThe reaction was stirred 3 hours
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted twice with ethyl acetate
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over calcium sulfate
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-163d0091c5fe4c9aafa784f27d41ab59
Source dataset
uspto-grants-1996_03
Patent number
US05498610

Reaction notes

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