4-Toluenesulfonyl chloride → HCID 12904513, compound

HRID 2174041Notes

Reaction equation

HRID 2174041 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)([O-:3])=[O:2].[H-].[Na+].[S:15](Cl)([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:17])=[O:16]>CN(C=O)C>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:15]([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:17])=[O:16])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 1457664-Nitro-1H-indole

Product 1

HCID 12904513HCID 12904513, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 4-nitro-1H-indole (CAS #: 4769-97-5) (10.4 g, 64.1 mmol) in DMF (401 mL) at 0° C. was added NaH (60% in mineral oil, 3.85 g, 96 mmol), and the mixture was stirred at 0° C. After 15 minutes, to the red suspension was added TsCl (14.67 g, 77 mmol). The reaction turned yellow and was warmed to room temperature. After 15 minutes the reaction was quenched by ice/H2O, and the mixture was stirred for 30 minutes at room temperature. The precipitate was collected by filtration to provide the title compound, which was used in the next reaction without any further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.43 (d, J=8.34 Hz, 1H) 8.15-8.29 (m, 2H) 7.96 (m, 2H) 7.60 (t, J=8.21 Hz, 1H) 7.42 (m, J=7.83 Hz, 2H) 7.26-7.38 (m, 1H) 2.33 (s, 3H)

Workup

  1. temperaturewas warmed to room temperature
  2. customAfter 15 minutes the reaction was quenched by ice/H2O
  3. stirringthe mixture was stirred for 30 minutes at room temperature
  4. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-5485614cd1fa44a69c941d8fff65ec34
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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