Ethyl Acetate → 851008-24-7

HRID 1891063Notes

Reaction equation

HRID 1891063 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[CH:6]=1)(=[NH:4])=[O:3].[OH-].[Na+].C(OCC)(=O)C>C1COCC1.Cl>[NH2:11][C:7]1[CH:6]=[C:5]([S:2]([CH3:1])(=[NH:4])=[O:3])[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 596740531-(S-Methanesulfonimidoyl)-3-nitrobenzene

Product 1

HCID 59674075851008-24-7

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 200 mg (1.00 mmol) of (RS)—S-methyl-S-(3-nitrophenyl)sulfoximide in 20 ml of THF is mixed at room temperature with 8 ml of an approximately 10% solution of Ti(III)Cl in 20-30% hydrochloric acid. After 3 hours, another 2 ml of the approximately 10% solution of Ti(III)Cl in 20-30% hydrochloric acid is added and stirred overnight at room temperature. The batch is made basic with 1N NaOH solution and mixed with ethyl acetate. It is filtered, and the filter cakes are washed with ethyl acetate/MeOH (3:2). The organic solvent is drawn off in a rotary evaporator, and the residue is extracted from ethyl acetate. The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. The residue that is obtained is purified by chromatography (DCM/EtOH 95:5). 82 mg (0.48 mmol, corresponding to 48% of theory) of the product is obtained.

Workup

  1. filtrationIt is filtered
  2. washthe filter cakes are washed with ethyl acetate/MeOH (3:2)
  3. customThe organic solvent is drawn off in a rotary evaporator
  4. extractionthe residue is extracted from ethyl acetate
  5. dry with materialThe combined organic phases are dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. customThe residue that is obtained
  9. customis purified by chromatography (DCM/EtOH 95:5)
  10. custom82 mg (0.48 mmol, corresponding to 48% of theory) of the product is obtained

Sources & evidence

ORD record
ord-4e3dc7f59bba46e0878b3d72ee17ccb5
Source dataset
uspto-grants-2013_08
Patent number
US08507510B2

Reaction notes

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