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

HRID 1184876Notes

Reaction equation

HRID 1184876 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:47][C:48]1[CH:54]=[CH:53][C:51]([NH2:52])=[CH:50][C:49]=1[N+:55]([O-:57])=[O:56]>CN(C=O)C>[CH3:47][C:48]1[CH:54]=[CH:53][C:51]([NH:52][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:1])([F:13])[F:12])[CH:4]=2)=[CH:50][C:49]=1[N+:55]([O-:57])=[O:56]

Participants

6

Reactant 4

HCID 83904-Methyl-3-nitroanilineHCID 99633-(Trifluoromethyl)benzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 11716802N-(4-Methyl-3-nitrophenyl)-3-(trifluoromethyl)benzamideYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3-(trifluoromethyl)benzoic acid (8 g, 42.1 mmol), HATU (19.20 g, 50.5 mmol) and DIPEA (13.91 mL, 84 mmol) in DMF (350 mL) was stirred for 15 min at rt. 4-methyl-3-nitroaniline (6.40 g, 42.1 mmol) was added and stirred overnight at 60° C. After cooling to room temperature the reaction was quenched with H2O. After stirring for 10 minutes the resulting precipitate was collected and washed with water to give compound N-(4-methyl-3-nitrophenyl)-3-(trifluoromethyl)benzamide 66 (12 g, 88%). (m/z)=325 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature the reaction
  2. customwas quenched with H2O
  3. stirringAfter stirring for 10 minutes the resulting precipitate
  4. customwas collected
  5. washwashed with water

Sources & evidence

ORD record
ord-0f8db148a9a34da894ff52fbb0d95c50
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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