Hydrochloric Acid → Teriflunomide

HRID 440314Notes

Reaction equation

HRID 440314 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH:13]=[N:14][O:15][C:16]=2[CH3:17])=[O:11])=[CH:5][CH:4]=1.[OH-].[Na+].Cl>CO.O>[F:1][C:2]([F:18])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:11])/[C:12](/[C:13]#[N:14])=[C:16](\[OH:15])/[CH3:17])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3899LeflunomideHCID 14798Sodium Hydroxide

Product 1

HCID 54684141Teriflunomide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

0.1 mol of N-(4-trifluoromethylphenyl)-5-methylisoxazole-4-carboxamide is dissolved in 100 ml of methanol and treated at +10° C. with a solution of 0.11 mol (4.4 g) of sodium hydroxide in 100 ml of water. The mixture is stirred for 30 minutes and, after diluting with water, is acidified with concentrated hydrochloric acid. The precipitated crop of crystals is filtered off with suction, washed with water and dried in air. The yield is 24.4 g of N-(4-trifluoromethylphenyl)-2-cyano-3-hydroxycrotonamide (compound 2). Melting point from methanol 205° to 206° C.

Workup

  1. filtrationThe precipitated crop of crystals is filtered off with suction
  2. washwashed with water
  3. customdried in air
  4. customfrom methanol 205° to 206° C.

Sources & evidence

ORD record
ord-e8066a485b564e0292c409521000f43c
Source dataset
uspto-grants-1996_05
Patent number
US05519042

Reaction notes

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