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

HRID 1369529Notes

Reaction equation

HRID 1369529 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](Cl)=[O:7].[N+:14]([C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[CH3:24])[NH2:20])([O-:16])=[O:15]>N1C=CC=CC=1>[CH3:24][C:23]1[CH:22]=[CH:21][C:19]([NH:20][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=2)=[CH:18][C:17]=1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 83904-Methyl-3-nitroanilineHCID 752573-(Trifluoromethyl)benzoyl chloride

Product 1

HCID 11716802N-(4-Methyl-3-nitrophenyl)-3-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-trifluoromethylbenzoyl chloride (9.9 ml), 3-nitro-4-methylaniline (10 g) and pyridine (100 ml) was stirred and heated to 80° C. for 2 hours. The reaction mixture was evaporated and the residue was triturated under 2N aqueous hydrochloric acid solution. The solid so obtained was isolated, washed in turn with a saturated aqueous sodium bicarbonate solution, water and isohexane and dried under vacuum at 55° C. to give N-(4-methyl-3-nitrophenyl)-3-trifluoromethylbenzamide as a solid (21.9 g); NMR Spectrum: (DMSOd6) 7.49 (d, 1H), 7.78 (m, 1H), 7.99 (m, 2H), 8.27 (m, 2H), 8.51 (s, 1H), 10.77 (s, 1H); Mass Spectrum: M−H− 323.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was triturated under 2N aqueous hydrochloric acid solution
  3. customThe solid so obtained
  4. customwas isolated
  5. washwashed in turn with a saturated aqueous sodium bicarbonate solution, water and isohexane
  6. customdried under vacuum at 55° C.

Sources & evidence

ORD record
ord-bc14bb8f149f4dddb46b508e094e7a3d
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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