Chloroform → 4-(Methylsulfinyl)aniline

HRID 351816Notes

Reaction equation

[CH3:1][S:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:18])C=1.C(Cl)(Cl)Cl>C(Cl)Cl>[CH3:1][S:2]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

20 g (143.66 mmol) of 4-methylthioaniline was placed in a flask and dissolved in 660 mL of CH2Cl2. The solution was cooled to 0° C. and 35.42 g (143.66 mmol) of m-chloroperbenzoic acid was added. The mixture was stirred for 3 h at room temperature and poured into CHCl3. It was then washed with saturated NaHCO3 solution, dried over MgSO4 and the solvent was removed, yielding a crude product that was purified by chromatography on silica gel, using MeOH/EtOAc/hexane mixtures of increasing polarity as eluent. The title compound of the example was obtained as a white solid (17.84 g, 80%).

Workup

washIt was then washed with saturated NaHCO3 solution
dry with materialdried over MgSO4
customthe solvent was removed

Sources & evidence

ORD record: ord-e8a8d2ac77b541d88a8e0b11e1abec61
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743816B2

Reaction notes

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