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

HRID 1391475Notes

Reaction equation

HRID 1391475 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-bd5c71daf31d4636bc9b4aad65e08c53
Source dataset
uspto-grants-2008_03
Patent number
US07338958B2

Reaction notes

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