Ethyl chloroformate → (RS)-N-(ethoxycarbonyl)-S-methyl-S-(4-nitrophenyl)sulfoximide

HRID 1891082Notes

Reaction equation

HRID 1891082 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]>N1C=CC=CC=1.[Na+].[Cl-]>[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 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 5234Sodium ChlorideSolvent

Procedure

8.50 g (42.5 mmol) of (RS)—S-(4-nitrophenyl)-S-methyl sulfoximide in 400 ml of pyridine is mixed drop by drop at room temperature with 18.8 ml (197.2 mmol) of ethyl chloroformate. The batch is stirred for 4 hours at room temperature and then added in dilute NaCl solution. It is extracted from ethyl acetate. The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (hexane/ethyl acetate 1:1). 8.94 g (32.8 mmol, corresponding to 77% of theory) of the product is obtained.

Workup

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

Sources & evidence

ORD record
ord-550c36d049e84076bdc148a15a0e950f
Source dataset
uspto-grants-2013_08
Patent number
US08507510B2

Reaction notes

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