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

HRID 1465024Notes

Reaction equation

HRID 1465024 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][C:8]=2[C:16]([F:19])([F:18])[F:17])[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH3:53][C:54]1[CH:60]=[CH:59][C:57]([NH2:58])=[CH:56][C:55]=1[N+:61]([O-:63])=[O:62]>CN(C)C=O.C(OCC)(=O)C>[CH3:53][C:54]1[CH:60]=[CH:59][C:57]([NH:58][C:11](=[O:13])[C:10]2[CH:14]=[CH:15][C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[C:8]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)=[CH:56][C:55]=1[N+:61]([O-:63])=[O:62]

Participants

7

Reactant 4

HCID 83904-Methyl-3-nitroanilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 594957964-Morpholin-4-yl-3-(trifluoromethyl)benzoic acid

Product 1

HCID 71269428N-(4-methyl-3-nitrophenyl)-4-morpholino-3-(trifluoromethyl)benzamideYield 97.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Morpholino-3-(trifluoromethyl)benzoic acid (694 mg, 2.523 mmol) was dissolved in dimethylformamide (5.6 mL), HATU (1.92 g, 5.047 mmol) and N,N-diisopropylethylamine (1.37 mL, 7.851 mmol) were added thereto and stirred at room temperature for 30 minutes. 4-Methyl-3-nitroaniline (256 mg, 1.682 mmol) was added to the reaction mixture and subjected to a reaction at 45° C. for 19 hours. After cooling to room temperature the reaction mixture was diluted with ethyl acetate (10 mL) and washed with an aqueous sodium hydrogen carbonate solution (10 mL). The organic layer was washed with water, dried with sodium sulfate, and the solvent was distilled under reduced pressure. The concentrated mixture was crystallized using ethyl acetate (3 mL) n-hexane (30 mL) to obtain the title compound (673 mg) as a brown solid.

Workup

  1. customsubjected to a reaction at 45° C. for 19 hours
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. washwashed with an aqueous sodium hydrogen carbonate solution (10 mL)
  4. washThe organic layer was washed with water
  5. dry with materialdried with sodium sulfate
  6. distillationthe solvent was distilled under reduced pressure
  7. customThe concentrated mixture was crystallized

Sources & evidence

ORD record
ord-9a8066dfbbf043beb66a1f455eed75fe
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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