4-Toluenesulfonyl chloride → HCID 86701531, compound

HRID 2173962Notes

Reaction equation

HRID 2173962 reaction equation
[CH3:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[NH:7][CH:6]=[CH:5]2.[H-].[Na+].[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>CN(C=O)C>[CH3:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([S:17]([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 533996595,7-Dimethyl-4-nitro-1H-indole

Product 1

HCID 86701531HCID 86701531, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5,7-dimethyl-4-nitro-1H-indole (CAS; 1190314-35-2, 10 g, 52.6 mmol) in DMF (200 mL) was added portionwise NaH (3.2 g, 60% in mineral oil, 79 mmol) at 0° C., and then the mixture was stirred at room temperature for 0.5 h. The mixture was cooled down to 0° C. To the red suspension was added TsCl (15.0 g, 79 mmol) at 0° C., and then the mixture was stirred at room temperature for 22 h. At this point, the reaction was quenched with half saturated aq. KHSO4 solution. The mixture was diluted with H2O, and then the whole mixture was stirred at room temperature for 1 h. The resulted solid was collected by filtration. The obtained brown solid was successively washed with H2O, MeOH, and heptane. The solid was dried to give the title compound. MS (ESI+) m/z 345.1 (M+H).

Workup

  1. temperatureThe mixture was cooled down to 0° C
  2. stirringthe mixture was stirred at room temperature for 22 h
  3. customAt this point, the reaction was quenched with half saturated aq. KHSO4 solution
  4. additionThe mixture was diluted with H2O
  5. stirringthe whole mixture was stirred at room temperature for 1 h
  6. filtrationThe resulted solid was collected by filtration
  7. washThe obtained brown solid was successively washed with H2O, MeOH, and heptane
  8. customThe solid was dried

Sources & evidence

ORD record
ord-ce160af88e2d4ca0bf6127b579c3e7ef
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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