Reaction equation
CC(O)=O.C(S[C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=1)C1C=CC=CC=1.[Cl:22]N1C(C)(C)C(=O)N(Cl)C1=O.[S:33](S([O-])=O)([O-:36])(=O)=[O:34].[Na+].[Na+]>C(Cl)Cl.O>[N+:19]([C:18]1[C:13]([S:33]([Cl:22])(=[O:36])=[O:34])=[N:14][CH:15]=[CH:16][CH:17]=1)([O-:21])=[O:20]Participants
Conditions
- Temperature
- 0 °C
Procedure
AcOH (6 ml) and water (12 ml) were added to a solution of 2-benzylsulfanyl-3-nitro-pyridine 437 (3.0 g, 12.2 mmol) in DCM (42 ml) and the mixture was cooled to 0° C. A suspension of 1,3-dichloro-5,5-dimethyl-imidazolidine-2,4-dione (7.20 g, 36.58 mmol) in DCM (24 ml) was added portionwise to the vigorously stirring solution. The mixture was allowed to slowly warm to 25° C. and stirring was continued for 16 h. The mixture was poured into 5% aq. sodium metabisulfite solution (50 ml) and the aqueous phase was extracted with DCM (100 ml). The organic phase was washed with water, sat. NaHCO3 solution and brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (2.7 g) which was used in the next step without further purification. The structure was confirmed by 1H NMR.
Workup
- additionwas added portionwise to the vigorously stirring solution
- temperatureto slowly warm to 25° C.
- extractionthe aqueous phase was extracted with DCM (100 ml)
- washThe organic phase was washed with water, sat. NaHCO3 solution and brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-ae600ed080864edbab166c47129b72c2
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102688B2
Linked notes
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