Pentachloropyridine → HCID 21331926, compound

HRID 1390924Notes

Reaction equation

HRID 1390924 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].[Cl:15][C:16]1[N:21]=[C:20]([Cl:22])[C:19]([Cl:23])=[C:18](Cl)[C:17]=1[Cl:25]>CN(C=O)C>[Cl:22][C:20]1[C:19]([Cl:23])=[C:18]([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:17]([Cl:25])=[C:16]([Cl:15])[N:21]=1

Participants

4

Reactant 2

HCID 16584PentachloropyridineHCID 671284-Nitro-alpha,alpha,alpha-trifluoro-o-toluidine

Product 1

HCID 21331926HCID 21331926, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (4.8 grams of 57% oil dispersion) was washed with pentane and 30 ml. of DMF was added under nitrogen. The slurry was stirred and cooled to 0° C. To this was added a solution of 4-nitro-2-trifluoromethylaniline (11.0 grams, 0.053 mole) in 20 ml. of DMF; the addition was carried out slowly, keeping the temperature of the reaction mixture below 10° C. The reaction mixture was stirred for one hour, slowly reaching room temperature. The reaction mixture was then cooled to 0° C., pentachloropyridine (10 grams; 0.059 mole) added, and the reaction mixture stirred for 72 hours, slowly reaching room temperature. A yellow solid crystallized. It was separated and recrystallized from ethanol. Elemental analysis showed:

Workup

  1. washSodium hydride (4.8 grams of 57% oil dispersion) was washed with pentane and 30 ml
  2. additionof DMF was added under nitrogen
  3. additionthe addition
  4. customthe temperature of the reaction mixture below 10° C
  5. stirringThe reaction mixture was stirred for one hour
  6. customslowly reaching room temperature
  7. temperatureThe reaction mixture was then cooled to 0° C.
  8. stirringthe reaction mixture stirred for 72 hours
  9. customslowly reaching room temperature
  10. customA yellow solid crystallized
  11. customIt was separated
  12. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e6da45b652a44d15bf55d9dcd4895b12
Source dataset
uspto-grants-1979_02
Patent number
US04140778

Reaction notes

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