4-Acetylbenzenesulfonyl chloride → 4-acetyl-N-(2,4-dimethylphenyl)-N-isobutylbenzenesulfonamide

HRID 1746438Notes

Reaction equation

HRID 1746438 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].[C:14]([C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1)(=[O:16])[CH3:15]>N1C=CC=CC=1>[C:14]([C:17]1[CH:18]=[CH:19][C:20]([S:23]([N:9]([C:3]2[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])[CH2:10][CH:11]([CH3:13])[CH3:12])(=[O:25])=[O:24])=[CH:21][CH:22]=1)(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 2664184-Acetylbenzenesulfonyl chlorideHCID 284223892,4-dimethyl-N-(2-methylpropyl)aniline

Product 1

HCID 867316024-acetyl-N-(2,4-dimethylphenyl)-N-isobutylbenzenesulfonamideYield 46.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of (2,4-dimethylphenyl)(2-methylpropyl)amine (300 mg, 1.692 mmol) in pyridine (5 mL), stirred in air at room temperature, was added 4-acetylbenzene-1-sulfonyl chloride (370 mg, 1.692 mmol) in one charge. The reaction mixture was stirred at 20° C. for 30 minutes, then left to stand overnight. The solvent was evaporated in vacuo then redissolved in methanol and passed through an aminopropyl (NH2) SPE cartridge, eluting with methanol, followed by 2M ammonia/methanol. The product containing fractions were combined and passed through a sulphonic acid (SCX) SPE cartridge eluting with methanol, followed by 2M ammonia/methanol. The product containing fractions were combined and evaporated under a stream of nitrogen to give the crude product. The crude was purified by flash (Si) chromatography (using a 0-50% ethyl acetate-cyclohexane gradient) to give the required product (282 mg) as a yellow gum. LCMS (M+1) 360, RT 1.35 mins.

Workup

  1. additioncharge
  2. waitleft
  3. waitto stand overnight
  4. customThe solvent was evaporated in vacuo
  5. dissolutionthen redissolved in methanol
  6. washeluting with methanol
  7. additionThe product containing fractions
  8. washeluting with methanol
  9. additionThe product containing fractions
  10. customevaporated under a stream of nitrogen
  11. customto give the crude product
  12. customThe crude was purified by flash (Si) chromatography (

Sources & evidence

ORD record
ord-076ce05b7cb24b22b6822f440d26476c
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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