2-Isopropenyl-5-(methylsulfonyl)aniline → 2-Isopropyl-5-(methylsulfonyl)aniline

Reaction equation

CS(C1C=CC(CCC)=C(C=1)N)(=O)=O.[C:15]([C:18]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][C:19]=1[NH2:20])([CH3:17])=[CH2:16]>>[CH:15]([C:18]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:21][C:19]=1[NH2:20])([CH3:17])[CH3:16]

Participants

Reactant 2

HCID 585219612-Isopropenyl-5-(methylsulfonyl)aniline2×

HCID 585220065-(Methylsulfonyl)-2-propylaniline

Product 1

HCID 283559112-Isopropyl-5-(methylsulfonyl)anilineYield 81%

Procedure

Following the general method as outlined in Intermediate 61, starting from 2-isopropenyl-5-(methylsulfonyl)aniline (Intermediate 89), the title compound was obtained as a green solid in 81% yield after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record: ord-e86db1a49f5f49c3a923685c1533ac4a
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273769B2

Reaction notes

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