4-Toluenesulfonyl chloride → HCID 86664379, compound

HRID 511846Notes

Reaction equation

HRID 511846 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH:12]=[O:13])[CH:5]=[CH:4]1.[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.[Cl-].[NH4+]>C1COCC1>[S:21]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH:12]=[O:13])[CH:5]=[CH:4]1)([C:18]1[CH:19]=[CH:20][C:15]([CH3:14])=[CH:16][CH:17]=1)(=[O:23])=[O:22]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2734629Indole-7-carboxaldehyde

Product 1

HCID 86664379HCID 86664379, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (240 mg, 5.9 mmol) in THF (10 mL) was added 1H-indole-7-carbaldehyde (570 mg, 3.9 mmol) at room temperature. After being stirred at room temperature for 20 min, 4-methylbenzene-1-sulfonyl chloride (1.1 g, 5.9 mmol) was added to the mixture. The mixture was stirred at room temperature for 1 hour. The mixture was poured into saturated ammonium chloride aqueous solution, and the aqueous phase was extracted with ethyl acetate (twice). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (4:1 (v/v)) to give 1.0 g (89% yield) of the title compound as a white solid:

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. extractionthe aqueous phase was extracted with ethyl acetate (twice)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (4:1 (v/v))

Sources & evidence

ORD record
ord-dc991f82da5f4050a2f0a70802c22a1f
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

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