N-[(R)-Cyclopropyl(4-nitrophenyl)oxidosulphanylidene]-2,2,2-trifluoroacetamide → N-[(R)-(4-Aminophenyl)(cyclopropyl)oxidosulphanylidene]-2,2,2-trifluoroacetamide

HRID 1027845Notes

Reaction equation

HRID 1027845 reaction equation
[CH:1]1([S:4]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)(=[N:6][C:7](=[O:12])[C:8]([F:11])([F:10])[F:9])=[O:5])[CH2:3][CH2:2]1>[Pd].C(O)C.C1COCC1>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([S:4]([CH:1]2[CH2:3][CH2:2]2)(=[N:6][C:7](=[O:12])[C:8]([F:11])([F:9])[F:10])=[O:5])=[CH:18][CH:17]=1

Participants

5

Reactant 1

HCID 56949254N-[(R)-Cyclopropyl(4-nitrophenyl)oxidosulphanylidene]-2,2,2-trifluoroacetamide

Product 1

HCID 58533486N-[(R)-(4-Aminophenyl)(cyclopropyl)oxidosulphanylidene]-2,2,2-trifluoroacetamideYield 93%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.4 g palladium on charcoal (10%/50% moisture) was added to a solution of 6.9 g (21.44 mmol) (RS)-S-cyclopropyl-S-(4-nitrophenyl)-N-(trifluoroacetyl)sulfoximide in 214 ml ethanol and 39 ml THF and was hydrogenated for 1 hour under normal pressure at 25° C. A further 1.4 g palladium on charcoal was added, and it was hydrogenated for a further 4.5 hours at normal pressure. The mixture was filtered, 1.4 g palladium on charcoal was added to the filtrate again and finally hydrogenated for 45 minutes. The mixture was filtered and concentrated by evaporation. 5.8 g (19.91 mmol; yield: 93%) of the product was obtained.

Workup

  1. waitit was hydrogenated for a further 4.5 hours at normal pressure
  2. filtrationThe mixture was filtered
  3. addition1.4 g palladium on charcoal was added to the filtrate again
  4. waitfinally hydrogenated for 45 minutes
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated by evaporation
  7. custom5.8 g (19.91 mmol; yield: 93%) of the product was obtained

Sources & evidence

ORD record
ord-dc659bd0e5c1491f95f98d8754562c31
Source dataset
uspto-grants-2014_05
Patent number
US08735412B2

Reaction notes

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