Formaldehyde → N,S-Dimethyl-S-(4-nitrophenyl)sulfoximine
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[NH:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:14]=O>C(O)=O>[CH3:14][N:12]=[S:10]([CH3:13])([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)=[O:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
500 mg (2.5 mmol) (RS)—S-(4-nitrophenyl)-S-methylsulfoximide in 4 ml formaldehyde (aqueous, 37%) and 20 ml formic acid (98-100%) are stirred in the open flask at 100° C. After 22 hours, the solvent is evaporated, the mixture is treated again with 4 ml formaldehyde (aqueous, 37%) and 20 ml formic acid (98-100%) and stirred for a further 22 hours at 100° C. Residues of the solvent are removed on the rotary evaporator. The remaining residue is dissolved with 2N HCl and extracted with dichloromethane. The aqueous phase is basified with NaHCO3 and extracted with dichloromethane. The combined organic phases are dried (Na2SO4), filtered and concentrated. 448 mg (2.1 mmol, corresponding to 85% of theor.) of the product is obtained.
Workup
- customthe solvent is evaporated
- additionthe mixture is treated again with 4 ml formaldehyde (aqueous, 37%) and 20 ml formic acid (98-100%)
- customResidues of the solvent are removed on the rotary evaporator
- dissolutionThe remaining residue is dissolved with 2N HCl
- extractionextracted with dichloromethane
- extractionextracted with dichloromethane
- dry with materialThe combined organic phases are dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- custom448 mg (2.1 mmol, corresponding to 85% of theor.) of the product is obtained
Sources & evidence
- ORD record
- ord-8d6326d28bb84f0f8b5f7f7838b8aadd
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524724B2
Reaction notes
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