Water → N-Benzoyl-3-(trifluoromethyl)-4-nitroaniline

HRID 2233231Notes

Reaction equation

HRID 2233231 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[NH2:6].[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.[OH-].[Na+]>N1C=CC=CC=1>[C:15]([NH:6][C:5]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:3]([C:2]([F:13])([F:14])[F:1])[CH:4]=1)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 949554-Nitro-3-(trifluoromethyl)aniline

Product 1

HCID 44203033N-Benzoyl-3-(trifluoromethyl)-4-nitroanilineYield 67.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-(trifluoromethyl)-4-nitroaniline (1.00 g, 4.85 mmol) and benzoyl chloride (0.62 ml, 5.34 mmol) were heated in pyridine (20 ml) at reflux for 3 hours under an inert atmosphere. The reaction was allowed to cool to ambient temperature, poured into water (200 ml) and basified by addition of 2.0 N aqueous sodium hydroxide solution. An oily liquid separated out which crystallised on standing at 4° C. overnight. The solid was collected by suction filtration, washed with water (3×20 ml) and then purified by flash chromatography on silica gel, eluting with dichloromethane. This yielded N-benzoyl 3-(trifluoromethyl)-4-nitroaniline (1.01 g, 67% yield) as a white solid:

Workup

  1. temperatureat reflux for 3 hours under an inert atmosphere
  2. customAn oily liquid separated out which
  3. customcrystallised
  4. filtrationThe solid was collected by suction filtration
  5. washwashed with water (3×20 ml)
  6. custompurified by flash chromatography on silica gel
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-7ae1344bc37d4895a035fb2835e65762
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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