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Water → 4-(Methylsulfonyl)-3-(trifluoromethyl)aniline

HRID 1597548
Notes
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Reaction equation

HRID 1597548 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[C:14]([F:17])([F:16])[F:15])(=[O:4])=[O:3].[Cl-].[NH4+].O>C(O)C.[Fe]>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[C:14]([F:15])([F:16])[F:17])(=[O:4])=[O:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 206051531-(Methylsulphonyl)-4-nitro-2-(trifluoromethyl)benzene

Product 1

HCID 223166824-(Methylsulfonyl)-3-(trifluoromethyl)anilineYield 76.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst
HCID 702
Ethanol
Solvent

Procedure

A mixture of 4-(methylsulfonyl)-3-(trifluoromethyl)nitrobenzene (1.55 g, 5.76 mmol), iron powder (1.61 g, 28.8 mmol), and ammonium chloride (0.031 g, 0.58 mmol) in ethanol (30 mL), and water (8 mL) was heated at reflux temperature for 1 hour. After cooling, insolubles were filtered off by Celite, and volatiles were removed by evaporation. The residue was redissolved in ethyl acetate (50 mL) and the whole washed with water and brine. After dried over MgSO4 and concentration in vacuo. The residue was washed with hexane to give the subtitle compound (1.05 g, 76.2%, yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 hour
  3. temperatureAfter cooling
  4. filtrationinsolubles were filtered off by Celite, and volatiles
  5. customwere removed by evaporation
  6. dissolutionThe residue was redissolved in ethyl acetate (50 mL)
  7. washthe whole washed with water and brine
  8. dry with materialAfter dried over MgSO4 and concentration in vacuo
  9. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-f4370d1535f34957ba05276f2367ccf1
Source dataset
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06294558B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes