3-Nitroaniline → 2-(3-trifluoromethylphenoxy)N-(3-nitrophenyl)nicotinamide

HRID 1679796Notes

Reaction equation

HRID 1679796 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:37])([F:36])[C:20]1[CH:21]=[C:22]([CH:33]=[CH:34][CH:35]=1)[O:23][C:24]1[N:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27]>C1(C)C=CC=CC=1>[F:36][C:19]([F:18])([F:37])[C:20]1[CH:21]=[C:22]([CH:33]=[CH:34][CH:35]=1)[O:23][C:24]1[N:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([NH:7][C:6]1[CH:8]=[CH:9][CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:27]

Participants

5

Reactant 3

HCID 74233-NitroanilineHCID 8471TriethylamineHCID 111624242-(3-Trifluoromethylphenoxy)nicotinoyl chloride

Product 1

HCID 128944062-(3-trifluoromethylphenoxy)N-(3-nitrophenyl)nicotinamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A solution of 1.5 grams (0.011 mole) 3-nitroaniline and 1.0 gram (0.011 mole) triethylamine in 100 milliliters toluene was placed in a flask. There was slowly added, with stirring, a solution of 3.2 grams (0.011 mole) 2-(3-trifluoromethylphenoxy) nicotinoyl chloride in 25 milliliters toluene. The rate of addition was controlled so as to maintain the temperature below 35° C. After the addition was complete the mixture was stirred at 45° C. for one hour, cooled, poured into 100 milliliters toluene, and washed with two 150-milliliter portions of water. The organic phase was separated, dried with magnesium sulfate, filtered and the solvent removed to produce 3.3 grams (73.3% of theoretical yield) of the desired product, m.p. 90°-95° C. The structure was confirmed by mass spectrometry.

Workup

  1. additionThere was slowly added
  2. additionThe rate of addition
  3. temperatureto maintain the temperature below 35° C
  4. additionAfter the addition
  5. stirringwas stirred at 45° C. for one hour
  6. temperaturecooled
  7. washwashed with two 150-milliliter portions of water
  8. customThe organic phase was separated
  9. dry with materialdried with magnesium sulfate
  10. filtrationfiltered
  11. customthe solvent removed
  12. customto produce

Sources & evidence

ORD record
ord-63b7610a4b5049fa84b211cb46f590eb
Source dataset
uspto-grants-1981_06
Patent number
US04270946

Reaction notes

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