4-Methyl-3-nitroaniline → N-(4-Methyl-3-nitrophenyl)-3-(trifluoromethyl)benzamide

HRID 1051248Notes

Reaction equation

HRID 1051248 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CCN(C(C)C)C(C)C.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27]>ClCCl>[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][CH:31]=[C:23]([C:22]([F:21])([F:32])[F:33])[CH:24]=2)=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 83904-Methyl-3-nitroanilineHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 11716802N-(4-Methyl-3-nitrophenyl)-3-(trifluoromethyl)benzamideYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methyl-3-nitroaniline (5 g, 32.9 mmol) was stirred in a solvent of dichloromethane (150 mL). The reaction solution was added with DIPEA (11.48 mL, 65.7 mmol) and 3-(trifluoromethyl)benzoylchloride (4.86 mL, 32.9 mmol), and stirred for about an hour at room temperature. The reaction mixture was washed with 1M aqueous HCl solution, an aqueous sodium bicarbonate and saline. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (10.6 g, 99%).

Workup

  1. washThe reaction mixture was washed with 1M aqueous HCl solution
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d01e32ac59a34659aa4a6326bbe8d9cb
Source dataset
uspto-grants-2016_07
Patent number
US09388165B2

Reaction notes

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