3-Nitroaniline → 4'-Trifluoromethyl-biphenyl-2-carboxylic acid (3-nitro-phenyl)-amide

HRID 431364Notes

Reaction equation

HRID 431364 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].C(N(CC)CC)C.[F:18][C:19]([F:36])([F:35])[C:20]1[CH:25]=[CH:24][C:23]([C:26]2[C:27]([C:32](Cl)=[O:33])=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:22][CH:21]=1>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][C:32]([C:27]2[C:26]([C:23]3[CH:24]=[CH:25][C:20]([C:19]([F:18])([F:35])[F:36])=[CH:21][CH:22]=3)=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:33])[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 74233-Nitroaniline2×HCID 8471TriethylamineHCID 110660004'-(Trifluoromethyl)-[1,1'-biphenyl]-2-carbonyl chloride

Product 1

HCID 101569574'-Trifluoromethyl-biphenyl-2-carboxylic acid (3-nitro-phenyl)-amideYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-nitroaniline (28.8 g, 209 mmol, 1 equiv) in THF (1000 mL, 35 volumes), was added triethylamine (70 mL, 500 mmol, 2.4 equiv). 3-Nitroaniline can be obtained from Aldrich, Milwaukee, Wis. A solution of 4′-trifluoromethyl-biphenyl-2-carbonyl chloride (71.3 g, 250 mmol, 1.2 equiv) in THF (250 mL, 3.5 volumes) was added dropwise over 30 minutes. The reaction was stirred at room temperature for 48 hours. The slurry was then filtered through diatomaceous earth and the filtrate was concentrated. Water (700 mL, 24 volumes) was added and the slurry was stirred at room temperature for 12 hours. The solids were collected by filtration and dried under vacuum at 40° C. to provide 4′-trifluoromethyl-biphenyl-2-carboxylic acid (3-nitro-phenyl)-amide (80.7 g, 100%) as a pale yellow powder.

Workup

  1. filtrationThe slurry was then filtered through diatomaceous earth
  2. concentrationthe filtrate was concentrated
  3. additionWater (700 mL, 24 volumes) was added
  4. stirringthe slurry was stirred at room temperature for 12 hours
  5. filtrationThe solids were collected by filtration
  6. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-40f204f55221432db511ed2a8cf033f3
Source dataset
uspto-grants-2003_12
Patent number
US06657065B2

Reaction notes

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