Water → 1-[Diazo(trifluoromethanesulfonyl)methanesulfonyl]-4-methylbenzene

HRID 1837410Notes

Reaction equation

[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([S:7]([CH2:10][S:11]([C:14]([F:17])([F:16])[F:15])(=[O:13])=[O:12])(=[O:9])=[O:8])=[CH:3][CH:2]=1.S([N:29]=[N+:30]=[N-])(C1C=CC(C)=CC=1)(=O)=O.C(N(CC)CC)C.O>C(#N)C>[C:1]1([CH3:18])[CH:2]=[CH:3][C:4]([S:7]([C:10]([S:11]([C:14]([F:16])([F:17])[F:15])(=[O:13])=[O:12])=[N+:29]=[N-:30])(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Crude p-toluenesulfonyl-trifluoromethanesulfonyl-methane (5 g, 0.017 mole) is dissolved in acetonitrile (200 ml) under nitrogen and the solution is cooled to 0° C. using an ice bath. Tosyl azide (16.3 g, 0.083 mole) and then triethylamine (4.6 ml, 0.063 mole) are added in one portion and the reaction mixture is stirred at that temperature for 24 h. After adding water (11), the mixture is extracted twice with dichloromethane (300 ml) and the combined organic phases are washed with 1 N HCl, saturated sodium bicarbonate and water. After drying over MgSO4 and removal of the solvent, the resulting yellow orange oil was chromatographed on silica gel using ethyl acetate/cyclohexane 1:5 as eluent, yielding p-toluenesulfonyl-trifluoromethanesulfonyl-diazomethane as a yellowish solid. The structure was confirmed by 1H/13C NMR and IR spectroscopy.

Workup

extractionthe mixture is extracted twice with dichloromethane (300 ml)
washthe combined organic phases are washed with 1 N HCl, saturated sodium bicarbonate and water
dry with materialAfter drying over MgSO4 and removal of the solvent
customthe resulting yellow orange oil was chromatographed on silica gel

Sources & evidence

ORD record: ord-83b64730d54a474b8a684bb0629e3fd7
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06783912B2

Reaction notes

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