4-(Benzyloxy)benzene-1-sulfonyl chloride → N-(2,4-dimethylphenyl)-N-(2-methylpropyl)-4-[(phenylmethyl)oxy]benzenesulfonamide

HRID 1487027Notes

Reaction equation

HRID 1487027 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]1([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>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:28]([C:25]1[CH:24]=[CH:23][C:22]([O:21][CH2:20][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:27][CH:26]=1)(=[O:30])=[O:29]

Participants

4

Reactant 2

HCID 47383854-(Benzyloxy)benzene-1-sulfonyl chlorideHCID 284223892,4-dimethyl-N-(2-methylpropyl)aniline

Product 1

HCID 89484270N-(2,4-dimethylphenyl)-N-(2-methylpropyl)-4-[(phenylmethyl)oxy]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To (2,4-dimethylphenyl)(2-methylpropyl)amine (1.00 g, 5.64 mmol) in pyridine (20 mL) was added 4-[(phenylmethyl)oxy]benzenesulfonyl chloride (1.754 g, 6.20 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo then redissolved in ethyl acetate and washed with a 10% solution of citric acid. At this stage a white precipitate formed and was isolated by filtration, LCMS analysis confirmed the precipitate was the desired product. The organic phase was then washed with 2 M NaOH and further precipitate was collected, again confirmed as the desired product by LCMS analysis. The organic phase was dried with magnesium sulfate, concentrated in vacuo and treated with dichloromethane to give a cloudy suspension, which was filtered to provide more of the desired product. Finally the filtrate was concentrated in vacuo and treated with methanol, whereupon additional product crystallised from the solution. The collected batches of product were combined (974 mg, 2.300 mmol) and used without further purification in the next step. LCMS [LCMS1] Rt 1.54 min, m/z (ES+) 424 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthen redissolved in ethyl acetate
  3. washwashed with a 10% solution of citric acid
  4. customAt this stage a white precipitate formed
  5. customwas isolated by filtration, LCMS analysis

Sources & evidence

ORD record
ord-6e22d73b5fd144ada99cc2bb1f20fc99
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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