4-Formylbenzene-1-sulfonyl chloride → N-(2,4-dimethylphenyl)-4-formyl-N-isobutylbenzenesulfonamide

HRID 1746436Notes

Reaction equation

HRID 1746436 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH:11]([CH3:13])[CH3:12].[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1)=[O:15]>N1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:10][CH:11]([CH3:13])[CH3:12])[S:22]([C:19]1[CH:18]=[CH:17][C:16]([CH:14]=[O:15])=[CH:21][CH:20]=1)(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 27592104-Formylbenzene-1-sulfonyl chlorideHCID 284223892,4-dimethyl-N-(2-methylpropyl)aniline

Product 1

HCID 86731601N-(2,4-dimethylphenyl)-4-formyl-N-isobutylbenzenesulfonamideYield 101.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of (2,4-dimethylphenyl)(2-methylpropyl)amine (400 mg, 2.256 mmol) in pyridine (5 mL), stirred in air at room temperature, was added 4-formylbenzene-1-sulfonyl chloride (760 mg, 3.71 mmol) in one charge. The reaction mixture was stirred at 20° C. for 30 minutes, then left to stand 6 hours. The solvent was removed in vacuo and the crude material purified by flash (Si) chromatography (using a 0-25% ethyl acetate-cyclohexane gradient). The appropriate fractions were combined and evaporated in vacuo to give the required product (794 mg) as a colourless gum. LCMS (M+1) 346, RT 1.33 mins.

Workup

  1. additioncharge
  2. waitleft
  3. waitto stand 6 hours
  4. customThe solvent was removed in vacuo
  5. customthe crude material purified by flash (Si) chromatography (
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-b2540e766edf46e9b56279484495528b
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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