Sodium Chloride → HCID 89262759, compound

HRID 2277742Notes

Reaction equation

HRID 2277742 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[N:5]=[S:6]([CH3:18])([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=1)=[O:7])[CH3:2].[OH-].[Na+].[Cl-].[Na+]>C1COCC1.[Cl-].[Ti+3].[Cl-].[Cl-]>[CH2:1]([O:3][C:4](=[O:19])[N:5]=[S:6]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=1)([CH3:18])=[O:7])[CH3:2]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 89262758HCID 89262758, compound

Product 1

HCID 89262759HCID 89262759, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Titanium(III)chloride solution (about 15% in about 10% hydrochloric acid, 118 mL; Merck Schuchardt OHG) was added to a stirred solution of (rac)-ethyl[methyl(3-nitrobenzyl)oxido-λ6-sulfanylidene]carbamate (5.0 g; 17.5 mmol) in THF (220 mL) at room temperature. The batch was stirred for 18 hours. By adding 2N sodium hydroxide solution the pH value of the reaction mixture, that was cooled with an ice bath, was raised to 8. The batch was saturated with solid sodium chloride and extracted with ethyl acetate (3×). The combined organic phases were washed with saturated aqueous sodium chloride solution, dried (sodium sulfate), filtered and concentrated to give the desired product (4.2 g) that was used without further purification.

Workup

  1. temperaturewas cooled with an ice bath
  2. temperaturewas raised to 8
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c5193abf4b3c40f9a8619a946e4a7b8a
Source dataset
uspto-grants-2015_09
Patent number
US09133171B2

Reaction notes

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