Dimethylformamide → N-(2,3,5,6-Tetrafluoro-4-pyridyl)-N-(4-nitro-2-trifluoromethylphenyl)amine

HRID 1390925Notes

Reaction equation

HRID 1390925 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=1)([O-:3])=[O:2].CN(C=O)C.[F:20][C:21]1[N:26]=[C:25]([F:27])[C:24]([F:28])=[C:23](F)[C:22]=1[F:30]>O>[F:27][C:25]1[C:24]([F:28])=[C:23]([NH:8][C:7]2[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[C:11]([F:12])([F:13])[F:14])[C:22]([F:30])=[C:21]([F:20])[N:26]=1

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 671284-Nitro-alpha,alpha,alpha-trifluoro-o-toluidineHCID 69690Pentafluoropyridine

Product 1

HCID 21331921N-(2,3,5,6-Tetrafluoro-4-pyridyl)-N-(4-nitro-2-trifluoromethylphenyl)amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (2.0 grams of 50% oil dispersion) was washed with pentane, filtered, and cooled to 0° C. A solution of 4-nitro-2-trifluoromethylaniline (6.1 grams; 0.030 mole) in 25 ml. of DMF was added over a five-minute period. The reaction mixture was allowed to stir for one hour, the temperature rising as high as 10° C. The reaction mixture was then cooled back down to 0° C. and pentafluoropyridine (5.0 grams; 0.030 mole) in 25 ml. of DMF was added. The reaction mixture was allowed to stir without further cooling for about sixteen hours, then poured over 1.8 liter of crushed ice and the volume adjusted to 1.8 liter with water. A precipitate formed and was allowed to remain in the reaction mixture for about twenty-four hours. The precipitate was then separated by filtration. It was recrystallized from ethanol, yielding 2.6 grams of a first crop (m.p. 104°-5° C.; U.S. Pat. No. 3,926,611 reports 107.7-108) and 3.0 grams of a second crop. Elemental analysis of the first crop showed

Workup

  1. washSodium hydride (2.0 grams of 50% oil dispersion) was washed with pentane
  2. filtrationfiltered
  3. customrising as high as 10° C
  4. stirringto stir
  5. temperaturewithout further cooling for about sixteen hours
  6. customA precipitate formed
  7. waitto remain in the reaction mixture for about twenty-four hours
  8. customThe precipitate was then separated by filtration
  9. customIt was recrystallized from ethanol
  10. customyielding 2.6 grams of a first crop (m.p. 104°-5° C.

Sources & evidence

ORD record
ord-996b3237571b463daf645a865761da61
Source dataset
uspto-grants-1979_02
Patent number
US04140778

Reaction notes

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