Sodium Chloride → (RS)-N-(ethoxycarbonyl)-S-methyl-S-(4-nitrophenyl)sulfoximide

HRID 1169710Notes

Reaction equation

HRID 1169710 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].Cl[C:15]([O:17][CH2:18][CH3:19])=[O:16].[Na+].[Cl-]>N1C=CC=CC=1>[CH2:18]([O:17][C:15]([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])=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 10928Ethyl chloroformateHCID 12463933S-Methyl-S-(4-nitrophenyl)sulfoximine

Product 1

HCID 59674069(RS)-N-(ethoxycarbonyl)-S-methyl-S-(4-nitrophenyl)sulfoximide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8.50 g (42.5 mmol) (RS)—S-(4-nitrophenyl)-S-methylsulfoximide in 400 ml pyridine are treated dropwise at room temperature with 18.8 ml (197.2 mmol) ethyl chloroformate. The mixture is stirred at room temperature for 4 hours and then poured into dilute NaCl solution. It is extracted with ethyl acetate. The combined organic phases are dried (Na2SO4), filtered and concentrated. The remaining residue is chromatographically purified (hexane/ethyl acetate 1:1). 8.94 g (32.8 mmol, corresponding to 77% of theor.) of the product is obtained.

Workup

  1. extractionIt is extracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe remaining residue is chromatographically purified (hexane/ethyl acetate 1:1)
  6. custom8.94 g (32.8 mmol, corresponding to 77% of theor.) of the product is obtained

Sources & evidence

ORD record
ord-b9d5b2217c4d4e20804ef159754ff226
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

Loading…