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

HRID 2199511Notes

Reaction equation

HRID 2199511 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>C(O)C.C1COCC1.[Pd]>[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

A solution of (RS)—S-cyclopropyl-S-(4-nitrophenyl)-N-(trifluoroacetyl)sulphoximide in ethanol and THF was admixed with palladium on carbon and hydrogenated for 1 hour under atmospheric pressure at 25° C. Palladium on carbon was added again and the mixture was hydrogenated for a further 4.5 hours at atmospheric pressure. The mixture was filtered, the filtrate was again admixed with palladium on carbon and finally hydrogenated for 45 minutes. The mixture was filtered and concentrated by evaporation (yield: 93%).

Workup

  1. filtrationThe mixture was filtered
  2. waitthe filtrate was again admixed with palladium on carbon and finally hydrogenated for 45 minutes
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated by evaporation (yield: 93%)

Sources & evidence

ORD record
ord-f8962c105ed94a9893ff4c656e0067b5
Source dataset
uspto-grants-2016_06
Patent number
US09359306B2

Reaction notes

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