Water → Ethyl [(4-aminophenyl)(methyl)oxido-sulfanylidene]carbamate

HRID 1891084Notes

Reaction equation

HRID 1891084 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]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl Acetate2×HCID 14798Sodium HydroxideHCID 59674069(RS)-N-(ethoxycarbonyl)-S-methyl-S-(4-nitrophenyl)sulfoximide

Product 1

HCID 44122615Ethyl [(4-aminophenyl)(methyl)oxido-sulfanylidene]carbamateYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8.70 g (32.0 mmol) of (RS)—N-(ethoxycarbonyl)-S-methyl-S-(4-nitrophenyl)sulfoximide in 650 ml of THF is slowly mixed at room temperature with 435 ml of a 10% solution of Ti(III)Cl in approximately 10% hydrochloric acid (Aldrich). The batch is stirred for 4 hours at room temperature and then cooled to 0° C. 450 ml of a 32% NaOH solution is added in drops. In this case, the reaction mixture is now diluted by the addition of water and ethyl acetate. It is mixed with 500 ml of ethyl acetate, and the organic phase is separated. The pulpy, aqueous phase is extracted from ethyl acetate. The combined organic phases are washed with dilute NaCl solution, dried (Na2SO4), filtered and concentrated by evaporation. 8.05 g (about 32.0 mmol) of the product is obtained, and said product is used without further purification.

Workup

  1. temperaturecooled to 0° C
  2. customthe organic phase is separated
  3. extractionThe pulpy, aqueous phase is extracted from ethyl acetate
  4. washThe combined organic phases are washed with dilute NaCl solution
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-896d8f4a81824f55937d87d0d5620201
Source dataset
uspto-grants-2013_08
Patent number
US08507510B2

Reaction notes

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