2,4-dimethyl-N-(2-methylpropyl)aniline → 4-bromo-N-(2,4-dimethylphenyl)-3,5-difluoro-N-isobutylbenzenesulfonamide

HRID 1487061Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 4-bromo-3,5-difluorobenzene-1-sulfonyl chloride (1462 mg, 5.02 mmol) in pyridine (10 mL) at 20° C. was added N-isobutyl-2,4-dimethylaniline (889 mg, 5.01 mmol) and the reaction mixture was stirred at 20° C. for 2 hours. The reaction mixture was then evaporated in vacuo and redissolved in ethyl acetate. The organic phase was washed with saturated sodium carbonate (25 mL), dried using a hydrophobic frit and evaporated in vacuo to give the required product as a yellow oil, 2.06 g. LCMS [LCMS2] Rt 1.57 min, m/z (ES+) 432/434 (M+H).

Workup

customThe reaction mixture was then evaporated in vacuo
dissolutionredissolved in ethyl acetate
washThe organic phase was washed with saturated sodium carbonate (25 mL)
customdried
customevaporated in vacuo

Sources & evidence

ORD record: ord-e36bc4801cae4e77bf7e2d48c28485fb
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428452B2

Reaction notes

Loading…