Benzenesulfonyl chloride → HCID 11109986, compound

HRID 1055403Notes

Reaction equation

HRID 1055403 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[Cl:7][C:8]1[NH:9][C:10]2[C:15]([C:16]=1[CH:17]=[O:18])=[CH:14][CH:13]=[CH:12][CH:11]=2.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C.[Cl-].[Na+].O>[Cl:7][C:8]1[N:9]([S:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:27])=[O:26])[C:10]2[C:15]([C:16]=1[CH:17]=[O:18])=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 10796Cesium carbonateHCID 3147912-chloro-1H-indole-3-carbaldehyde

Product 1

HCID 11109986HCID 11109986, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

Cs2CO3 (996 mg, 3.06 mmol) was added to a solution of 2-chloro-1H-indole-3-carbaldehyde (0.5 g, 2.78 mmol) and benzene sulfonyl chloride (0.39 mL, 3.06 mmol) in DMF (5 mL) and the mixture heated to 60° C. After 3 h the mixture was diluted with brine and extracted with EtOAc. The combined extracts were dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography to afford 2-chloro-1-(phenylsulfonyl)-1H-indole-3-carbaldehyde (33 mg, 5%) as a white solid.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a7980003f073423aac7eb16fa2b41b02
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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