4-(Trifluoromethyl)aniline → Leflunomide

HRID 2396699Notes

Reaction equation

HRID 2396699 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>[CH3:1][C:2]1[O:6][N:5]=[CH:4][C:3]=1[C:7]([NH:16][C:15]1[CH:17]=[CH:18][C:12]([C:11]([F:10])([F:19])[F:20])=[CH:13][CH:14]=1)=[O:8]

Participants

4

Reactant 2

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

Product 1

HCID 3899LeflunomideYield 94.7%

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 dropwise 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. 12.8 g of white crystalline 5-methylisoxazole-4-carboxylic acid (4-trifluoromethyl)-anilide (compound 1) are thus obtained.

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

Sources & evidence

ORD record
ord-b96bfd505522497987acb20462baec4e
Source dataset
uspto-grants-1996_02
Patent number
US05494911

Reaction notes

Loading…