4-(Trifluoromethyl)aniline → Leflunomide

HRID 440313Notes

Reaction equation

HRID 440313 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[CH:4][C:3]=1[C:7](Cl)=[O:8].[F:10][C:11]([F:20])([F:19])[C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1>C(#N)C>[F:10][C:11]([F:19])([F:20])[C:12]1[CH:13]=[CH:14][C:15]([NH:16][C:7]([C:3]2[CH:4]=[N:5][O:6][C:2]=2[CH3:1])=[O:8])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 27599175-Methyl-1,2-oxazole-4-carbonyl chloride

Product 1

HCID 3899Leflunomide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 0.05 mol of 5-methylisoxazole-4-carbonyl chloride (7.3 g) in 20 ml of acetonitrile is added drop wise at room temperature to a solution of 0.1 mol of 4-trifluoromethylaniline (16.1 g)in 150 ml of acetonitrile. After stirring for 20 minutes, the precipitated 4-trifluoromethylaniline hydrochloride is filtered off with suction and washed twice with 20 ml of acetonitrile each time, and the combined filtrates are concentrated under reduced pressure. The yield is 12.8 g of white, crystalline N-(4-trifluoromethylphenyl)-5-methylisoxazole-4-carboxamide (compound 1). Melting point from toluol 166,5° C.

Workup

  1. filtrationthe precipitated 4-trifluoromethylaniline hydrochloride is filtered off with suction
  2. washwashed twice with 20 ml of acetonitrile each time
  3. concentrationthe combined filtrates are concentrated under reduced pressure
  4. customfrom toluol 166,5° C.

Sources & evidence

ORD record
ord-b10f22d4a13d467b9899865577a76d89
Source dataset
uspto-grants-1996_05
Patent number
US05519042

Reaction notes

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