Styrene-4-sulfonyl chloride → N-(4-ethylphenyl)-N-isobutyl-4-vinylbenzenesulfonamide

HRID 1487078Notes

Reaction equation

HRID 1487078 reaction equation
[CH2:1]([C:3]1[CH:13]=[CH:12][C:6]([NH:7][CH2:8][CH:9]([CH3:11])[CH3:10])=[CH:5][CH:4]=1)[CH3:2].[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1)=[CH2:15]>N1C=CC=CC=1>[CH2:1]([C:3]1[CH:13]=[CH:12][C:6]([N:7]([CH2:8][CH:9]([CH3:10])[CH3:11])[S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH:14]=[CH2:15])=[CH:17][CH:18]=2)(=[O:24])=[O:23])=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 9855777Styrene-4-sulfonyl chlorideHCID 284793854-ethyl-N-(2-methylpropyl)aniline

Product 1

HCID 89876082N-(4-ethylphenyl)-N-isobutyl-4-vinylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 4-ethyl-N-isobutylaniline (400 mg, 2.256 mmol) in pyridine (5 mL) stirred in air at room temperature was added 4-vinylbenzene-1-sulfonyl chloride (760 mg, 3.75 mmol) in one charge. The reaction mixture was stirred at 20° C. for 30 minutes then stood for 16 hours. The solvent was evaporated in vacuo (Vaportec V10) to give the crude product, which was then purified by silica (Si) chromatography (0-50% ethyl acetate-cyclohexane gradient). The appropriate fractions were combined and evaporated in vacuo to give the required product, 940 mg, as a colourless gum. LCMS [LCMS1] Rt 1.44 min, m/z (ES+) 344 (M+H).

Workup

  1. additioncharge
  2. waitthen stood for 16 hours
  3. customThe solvent was evaporated in vacuo (Vaportec V10)
  4. customto give the crude product, which
  5. customwas then purified by silica (Si) chromatography (0-50% ethyl acetate-cyclohexane gradient)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-579fe86de9f74e41b83d567f1d5cab48
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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