Ammonium formate → N-(3-amino-5-trifluoromethyl-phenyl)-methanesulfonamide

HRID 1957955Notes

Reaction equation

HRID 1957955 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-])=O.C([O-])=O.[NH4+]>O1CCOCC1.ClCCl.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:7]=[C:8]([C:10]([F:13])([F:11])[F:12])[CH:9]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 68424558N-[3-nitro-5-(trifluoromethyl)phenyl]methanesulfonamide

Product 1

HCID 21961371N-(3-amino-5-trifluoromethyl-phenyl)-methanesulfonamide

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

N-(3-nitro-5-trifluoromethyl-phenyl)-methylsulfonamide (0.1 g; 0.4 mmol) ammonium formate (0.1 g; 1.8 mmol) and Raney-Nickel (16 mg) were dissolved in 0.4 mL of dioxane. The reaction was heated to 140° C. for 6 minutes in a micro wave reactor. The mixture was then diluted with dichloromethane, filtrated and the filtrate concentrated. 70 mg (0.27 mmol; 68% yield) of an orange oil were obtained.

Workup

  1. filtrationfiltrated
  2. concentrationthe filtrate concentrated
  3. custom70 mg (0.27 mmol; 68% yield) of an orange oil were obtained

Sources & evidence

ORD record
ord-acd2e04d3f67409283ddcfaa6af32f72
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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