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

HRID 238131Notes

Reaction equation

HRID 238131 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 (4.5 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-743bb345b7c342fbb5e13e52c4e02efa
Source dataset
uspto-grants-2014_02
Patent number
US08642611B2

Reaction notes

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