4-(Trifluoromethyl)aniline → HCID 13121219, compound

HRID 544388Notes

Reaction equation

HRID 544388 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1>>[CH3:8][C:7]1[C:2]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][CH:12]=2)=[N:3][CH:4]=[N:5][C:6]=1[CH3:9]

Participants

3

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 126003894-Chloro-5,6-dimethylpyrimidine

Product 1

HCID 13121219HCID 13121219, compoundYield 24%

Procedure

To 4.3 g (0.03 mole) of 4-chloro-5,6-dimethylpyrimidine were added 4.8 g (0.03 mole) of p-aminobenzotrifluoride; the mixture was then heated at 100°-150° C. for about 3 minutes. The reaction mixture quickly became a solution and soon produced a precipitate which was separated and then made alkaline by the addition of 50 ml of a dilute aqueous solution of sodium hydroxide. The insolubles were collected by filtration, washed with water and then recrystallised from a 7:3 by volumemixture of ethanol and water, to give 1.2 g (yield 24%) of the desired Compound No. 38 in the form of a pale brown powder melting at 137°-139° C.

Workup

  1. temperaturethe mixture was then heated at 100°-150° C. for about 3 minutes
  2. customsoon produced a precipitate which
  3. customwas separated
  4. additionby the addition of 50 ml of a dilute aqueous solution of sodium hydroxide
  5. filtrationThe insolubles were collected by filtration
  6. washwashed with water
  7. customrecrystallised from a 7:3 by volumemixture of ethanol and water

Sources & evidence

ORD record
ord-e96c509cda154b948c690e592f4f6825
Source dataset
uspto-grants-1984_05
Patent number
US04450162

Reaction notes

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