2,4-dimethyl-N-(2-methylpropyl)aniline → methyl 5-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)-2-methoxybenzoate

HRID 1487073Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred solution of methyl 5-(chlorosulfonyl)-2-methoxybenzoate (1 g, 3.78 mmol) in pyridine (3 mL) at 25° C. was added N-isobutyl-2,4-dimethylaniline (0.670 g, 3.78 mmol) and the reaction mixture stirred at 25° C. for 2 hours, then stood for 12 hours. The pyridine was evaporated in vacuo to give a yellow oil which was purified by silica (Si) chromatography (0-50% ethyl acetate-cyclohexane). The appropriate fractions were combined and evaporated in vacuo to give the required product, 1.485 g, as a colourless oil. LCMS [LCMS2] Rt 1.37 min, m/z (ES+) 406 (M+H).

Workup

waitstood for 12 hours
customThe pyridine was evaporated in vacuo
customto give a yellow oil which
customwas purified by silica (Si) chromatography (0-50% ethyl acetate-cyclohexane)
customevaporated in vacuo

Sources & evidence

ORD record: ord-ee57119302db4885b6249df8304cc4d9
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428452B2

Reaction notes

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