Sodium Bicarbonate → 2-Methyl-5-(pentafluorosulfur)aniline

HRID 2223440Notes

Reaction equation

HRID 2223440 reaction equation
Cl[CH:2](Cl)[C:3]1[CH:8]=[CH:7][C:6]([S:9]([F:14])([F:13])([F:12])([F:11])[F:10])=[CH:5][C:4]=1[N+:15]([O-])=O.C([O-])(O)=O.[Na+]>COCCOC.[Pd]>[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([F:11])([F:10])([F:13])([F:14])[F:12])=[CH:5][C:4]=1[NH2:15]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 533430391-Nitro-2-dichloromethyl-5-(pentafluorosulfanyl)benzene

Product 1

HCID 665235072-Methyl-5-(pentafluorosulfur)anilineYield 78.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

2.0 g of 1-dichloromethyl-2-nitro-4-pentafluorosulfanylbenzene were dissolved in 25 ml of DME and, after addition of 200 mg of Pd/C (5%) and 100 ml of a saturated aqueous NaHCO3 solution, hydrogenated under 5 bar of H2 for 54 hours. The catalyst was then removed by filtration and the reaction solution was extracted 3 times with 50 ml of MTB each time. Drying over MgSO4 was followed by removal of the solvent in vacuo. 1.1 g of a colorless oil were obtained.

Workup

  1. customThe catalyst was then removed by filtration
  2. extractionthe reaction solution was extracted 3 times with 50 ml of MTB each time
  3. dry with materialDrying over MgSO4
  4. customwas followed by removal of the solvent in vacuo

Sources & evidence

ORD record
ord-06ed95ef58ca4abfad846c70405ff9da
Source dataset
uspto-grants-2008_05
Patent number
US07375138B2

Reaction notes

Loading…