Hydrochloric Acid → (RS)-S-(4-aminophenyl)-S-cyclopropyl-N-[2-(trimethylsilyl)ethylsulfonyl]sulfoximide

HRID 1391469Notes

Reaction equation

HRID 1391469 reaction equation
[CH:1]1([S:4]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)(=[N:6][S:7]([CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])(=[O:9])=[O:8])=[O:5])[CH2:3][CH2:2]1.Cl.[OH-].[Na+].C(OCC)(=O)C>O1CCCC1.[Cl-].[Ti+3].[Cl-].[Cl-]>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([S:4]([CH:1]2[CH2:3][CH2:2]2)(=[N:6][S:7]([CH2:10][CH2:11][Si:12]([CH3:14])([CH3:15])[CH3:13])(=[O:8])=[O:9])=[O:5])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 59252685(RS)-S-cyclopropyl-S-(4-nitrophenyl)-N-[2-(trimethylsilyl)ethyl-sulfonyl]sulfoximide

Product 1

HCID 59674073(RS)-S-(4-aminophenyl)-S-cyclopropyl-N-[2-(trimethylsilyl)ethylsulfonyl]sulfoximideYield 72.8%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

320 mg of (RS)-S-cyclopropyl-S-(4-nitrophenyl)-N-[2-(trimethylsilyl)ethyl-sulfonyl]sulfoximide is dissolved in 5 ml of tetrahydrofuran. While being cooled with ice, 7.2 ml of an approximately 10% by weight solution of titanium(III) chloride in 20-30% by weight of hydrochloric acid is added in drops. The solution is stirred for 16 hours at room temperature and poured onto ice. The pH is set at 8-9 with 15% sodium hydroxide solution. After ethyl acetate is added, the mixture is vigorously stirred. The precipitate is suctioned off and washed with 100 ml of ethyl acetate. The filtrates are combined, dried and concentrated by evaporation. After purification by flash chromatography, 215 mg of (RS)-S-(4-aminophenyl)-S-cyclopropyl-N-[2-(trimethylsilyl)ethylsulfonyl]sulfoximide is obtained.

Workup

  1. additionis added in drops
  2. additionpoured onto ice
  3. stirringthe mixture is vigorously stirred
  4. washwashed with 100 ml of ethyl acetate
  5. customdried
  6. concentrationconcentrated by evaporation
  7. customAfter purification by flash chromatography

Sources & evidence

ORD record
ord-1211b6a0311a41318472999831ea6f10
Source dataset
uspto-grants-2008_03
Patent number
US07338958B2

Reaction notes

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