Dimethyl Sulfoxide → 2-trifluoromethylphenyl-S,S-dimethylsulfilimine

HRID 483280

Reaction equation

[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N+:9]([O-])=O.FC(F)(F)C1C=CC=CC=1N=C=O.[CH3:27][S:28]([CH3:30])=O>>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]=[S:28]([CH3:30])[CH3:27]

Participants

Reactant 3

HCID 679Dimethyl Sulfoxide

HCID 97952-Nitro-alpha,alpha,alpha-trifluorotoluene

HCID 167942-(Trifluoromethyl)phenyl isocyanate

Product 1

HCID 133911922-trifluoromethylphenyl-S,S-dimethylsulfilimine

Procedure

The process of claim 18 in which 2-trifluoromethylnitrobenzene is carbonylated to 2-trifluoromethylphenyl isocyanate, which is reacted with dimethylsulfoxide to obtain N-(2-trifluoromethylphenyl)-S,S-dimethylsulfilimine, rearranged to a 2-(methylthiomethyl)-6-trifluoromethylaniline, and desulfurized to 2-methyl-6-trifluoromethyl aniline.

Sources & evidence

ORD record: ord-564a0531b1c74f918c075c91dda58357
Source dataset: uspto-grants-1986_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04578514

Linked notes

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