Water → HCID 22677140, compound

HRID 1837411Notes

Reaction equation

S1C=CC=C1S(C[S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11])(=O)=O.[S:17](N=[N+]=[N-])([C:20]1C=CC(C)=[CH:22][CH:21]=1)(=O)=O.C([N:32]([CH2:35][CH3:36])CC)C.O.C(#[N:40])C>ClCCl>[S:17]1[CH:20]=[CH:21][CH:22]=[C:36]1[C:35]([S:10]([C:13]([F:14])([F:15])[F:16])(=[O:11])=[O:12])=[N+:32]=[N-:40]

Participants

Conditions

Temperature: 0 °C

Procedure

Crude 2-thienylsulfonyl-trifluoromethanesulfonyl-methane (5.6 g, 0.019 mole) is dissolved in acetonitrile (250 ml) under nitrogen and the solution is cooled to 0° C. using an ice bath. Tosyl azide (18.76 g, 0.095 mole) and then triethylamine (5.3 ml, 0.038 mole) are added in one portion and the reaction mixture is stirred at that temperature for 24 h. After adding water (450 ml) and dichloromethane (200 ml), the phases are separated and the aqueous layer is extracted twice with dichloromethane (150 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 crude product is obtained as orange oil, which was chromatographed on silica gel using ethyl acetate/cyclohexane 1:4 as eluent, yielding 2-thienyl-trifluoromethanesulfonyl-diazomethane as a yellowish solid (400 mg, 6.5%). The structure was confirmed by 1H/13C NMR and IR spectroscopy.

Workup

customthe phases are separated
extractionthe aqueous layer is extracted twice with dichloromethane (150 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 crude product is obtained as orange oil, which
customwas chromatographed on silica gel

Sources & evidence

ORD record: ord-a08a45a3f8c746c49d788bee8c26fe55
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06783912B2

Reaction notes

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