Water → Ethyl [(4-aminophenyl)(methyl)oxido-sulfanylidene]carbamate
Reaction equation
[CH2:1]([O:3][C:4]([N:6]=[S:7]([CH3:18])([C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)=[O:8])=[O:5])[CH3:2].[OH-].[Na+].O.C(OCC)(=O)C>C1COCC1.Cl>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([S:7]([CH3:18])(=[N:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:8])=[CH:10][CH:11]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 8.70 g (32.0 mmol) (RS)—N-(ethoxycarbonyl)-S-methyl-S-(4-nitro-phenyl)sulfoximide in 650 ml THF is slowly treated at room temperature with 435 ml of a 10% solution of Ti(III)Cl3 in approximately 10% hydrochloric acid (Aldrich). The mixture is stirred at room temperature for 4 hours and then cooled to 0° C. 450 ml of a 32% NaOH solution are added dropwise. During this, the reaction mixture is periodically diluted by the addition of water and ethyl acetate. It is treated with 500 ml ethyl acetate and the organic phase is separated. The mushy aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with dilute NaCl solution, dried (Na2SO4), filtered and concentrated. 8.05 g (ca. 32.0 mmol) of the product is obtained, which is used without further purification.
Workup
- temperaturecooled to 0° C
- customthe organic phase is separated
- extractionThe mushy aqueous phase is extracted with ethyl acetate
- washThe combined organic phases are washed with dilute NaCl solution
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-512be9e4dc534add8a54083bfaca7446
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642611B2
Reaction notes
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