Diisopropyl Ether → (RS)-S-(4-Aminophenyl)-S-methyl-N-(trifluoroacetyl)sulfoximide

HRID 1027851Notes

Reaction equation

HRID 1027851 reaction equation
[CH3:1][S:2]([C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)(=[N:4][C:5](=[O:10])[C:6]([F:9])([F:8])[F:7])=[O:3].C(OC(C)C)(C)C>[Pd].C(O)C.C1COCC1>[NH2:17][C:14]1[CH:13]=[CH:12][C:11]([S:2]([CH3:1])(=[N:4][C:5](=[O:10])[C:6]([F:9])([F:7])[F:8])=[O:3])=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 7914Diisopropyl EtherHCID 58533487(RS)-S-Methyl-S-(4-nitrophenyl)-N-(trifluoroacetyl)sulfoximide

Product 1

HCID 58533493(RS)-S-(4-Aminophenyl)-S-methyl-N-(trifluoroacetyl)sulfoximideYield 89%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

292 mg palladium on charcoal (10%/50% moisture) was added to a solution of 1.34 g (4.52 mmol) (RS)-S-methyl-S-(4-nitrophenyl)-N (trifluoroacetyl)sulfoximide in 45 ml ethanol and 8 ml THF and was hydrogenated for 45 minutes under normal pressure at 24° C. The mixture was filtered and concentrated by evaporation. The residue obtained was stirred with diisopropyl ether. The solid was filtered off with suction and dried. 1.07 g (4.03 mmol; yield: 89%) of the product was obtained.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated by evaporation
  3. customThe residue obtained
  4. filtrationThe solid was filtered off with suction
  5. customdried
  6. custom1.07 g (4.03 mmol; yield: 89%) of the product was obtained

Sources & evidence

ORD record
ord-26d6a54abc5746bc912cbca0b58fcaa0
Source dataset
uspto-grants-2014_05
Patent number
US08735412B2

Reaction notes

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