2,3-Dimethylaniline → 2,3-Dimethyl-(1-thiaethyl)-benzene

HRID 49684

Reaction equation

N(OC(C)(C)C)=O.[CH3:8][C:9]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:10]=1N.[CH3:17][S:18]SC>[Cu]>[CH3:8][C:9]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:10]=1[S:18][CH3:17]

Participants

Conditions

Temperature: 77.5 °C

Procedure

355 g (3.44 mol) of tert-butyl nitrite and 250 g of copper powder (3.9 mol) are initially charged in 1250 ml of dimethyl disulfide, and a solution of 250 g (2.07 mol) of 2,3-dimethylaniline in 1000 ml of dimethyl disulfide is added dropwise at 50-52° C. The mixture is subsequently stirred at 75-80° C. for 1.5 hours. For work-up, the mixture is cooled, filtered off with suction through kieselguhr, and the filtrate is washed with saturated aqueous NaHCO3 solution. For the purification of the product, the organic phase is separated by distillation. Initially, excess dimethyl disulfide is removed at atmospheric pressure. 1446 g of dimethyl disulfide (purity>97% according to GC) are recovered. The residue is then subjected to fractional distillation under reduced pressure (0.1 mbar).

Workup

temperatureFor work-up, the mixture is cooled
filtrationfiltered off with suction through kieselguhr
washthe filtrate is washed with saturated aqueous NaHCO3 solution
customFor the purification of the product
customthe organic phase is separated by distillation
customInitially, excess dimethyl disulfide is removed at atmospheric pressure
custom1446 g of dimethyl disulfide (purity>97% according to GC) are recovered
distillationThe residue is then subjected to fractional distillation under reduced pressure (0.1 mbar)

Sources & evidence

ORD record: ord-f14d107e81204a399d3161868f91fb0d
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706886B2

Linked notes

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