Aniline → HCID 7033676, compound

HRID 2172689Notes

Reaction equation

HRID 2172689 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1.CCOC(C)=O.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 2

HCID 6115AnilineHCID 394974-Cyanobenzenesulfonyl chloride

Product 1

HCID 7033676HCID 7033676, compoundYield 65.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-cyanobenzene-1-sulfonyl chloride (200 mg, 0.992 mmol) in pyridine (4960 μL) was added aniline (100 μL, 1.091 mmol) and the reaction mixture stirred overnight at rt. The reaction mixture was diluted with EtOAc and water+0.1N HCl. The phases were separated, the aqueous phase extracted and the combined organic layers washed with 0.1N HCl and brine. After drying over magnesium sulfate, the solution was concentrated under vacuum to yield 4-cyano-N-phenyl-benzenesulfonamide 198 mg (0.652 mmol) of yellow oil.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase extracted
  3. washthe combined organic layers washed with 0.1N HCl and brine
  4. dry with materialAfter drying over magnesium sulfate
  5. concentrationthe solution was concentrated under vacuum

Sources & evidence

ORD record
ord-4d7959f17c8a490097157d3689901381
Source dataset
uspto-grants-2015_06
Patent number
US09056843B2

Reaction notes

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