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) of (RS)—S-(4-nitrophenyl)-S-methyl sulfoximide in 4 ml of formaldehyde (aqueous, 37%) and 20 ml of formic acid (98-100%) are stirred in an open flask at 100° C. After 22 hours, the solvent is evaporated, mixed again with 4 ml of formaldehyde (aqueous, 37%) and 20 ml of formic acid (98-100%) and stirred for another 22 hours at 100° C. Residue from the solvent is drawn off in a rotary evaporator. The remaining residue is dissolved with 2N HCl and extracted from DCM. The aqueous phase is made basic with NaHCO3 and extracted from DCM. The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. 448 mg (2.1 mmol, corresponding to 85% of theory) of the product is obtained.
Workup
- customthe solvent is evaporated
- additionmixed again with 4 ml of formaldehyde (aqueous, 37%) and 20 ml of formic acid (98-100%)
- customResidue from the solvent is drawn off in a rotary evaporator
- dissolutionThe remaining residue is dissolved with 2N HCl
- extractionextracted from DCM
- extractionextracted from DCM
- dry with materialThe combined organic phases are dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated by evaporation
- custom448 mg (2.1 mmol, corresponding to 85% of theory) of the product is obtained
Sources & evidence
- ORD record
- ord-f7b9e699f289418ab8ab91018c1350d0
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507510B2
Reaction notes
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