4-((3,5-Dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chloride → 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(4-ethylphenyl)-N-isobutylbenzenesulfonamide

HRID 1746421Notes

Reaction equation

HRID 1746421 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].[CH3:14][C:15]1[C:19]([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)=[C:18]([CH3:32])[O:17][N:16]=1>N1C=CC=CC=1>[CH3:14][C:15]1[C:19]([CH2:20][O:21][C:22]2[CH:23]=[CH:24][C:25]([S:28]([N:7]([C:6]3[CH:12]=[CH:13][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=3)[CH2:8][CH:9]([CH3:10])[CH3:11])(=[O:30])=[O:29])=[CH:26][CH:27]=2)=[C:18]([CH3:32])[O:17][N:16]=1

Participants

4

Reactant 2

HCID 164907024-((3,5-Dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chlorideHCID 284793854-ethyl-N-(2-methylpropyl)aniline

Product 1

HCID 715434874-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(4-ethylphenyl)-N-isobutylbenzenesulfonamideYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 4-ethyl-N-isobutylaniline (50 mg, 0.282 mmol) in pyridine (1 mL) was added 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}benzenesulfonyl chloride (94 mg, 0.310 mmol) and the reaction stood at room temperature, in air, for 16 hours. The crude was then purified by MDAP (Method F), to provide 103.6 mg of desired product. LCMS (M+1) 443, RT 1.39 mins.

Workup

  1. customThe crude was then purified by MDAP (Method F)

Sources & evidence

ORD record
ord-4112b51de7e14304960be5b5953077f5
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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