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

HRID 38200Notes

Reaction equation

HRID 38200 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-190162474c0549a8bda2085be934b64b
Source dataset
uspto-grants-2013_09
Patent number
US08524724B2

Reaction notes

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