4-(Trifluoromethyl)aniline → Teriflunomide

HRID 1943100Notes

Reaction equation

HRID 1943100 reaction equation
C(O[C:4](=[O:11])[C:5]([C:9]#[N:10])=[C:6]([OH:8])[CH3:7])C.[F:12][C:13]([F:22])([F:21])[C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1>C1(C)C(C)=CC=CC=1>[CH3:7]/[C:6](/[OH:8])=[C:5](/[C:4]([NH:18][C:17]1[CH:16]=[CH:15][C:14]([C:13]([F:12])([F:21])[F:22])=[CH:20][CH:19]=1)=[O:11])\[C:9]#[N:10]

Participants

4

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 761797102-Butenoic acid, 2-cyano-3-hydroxy-, ethyl ester

Product 1

HCID 54684141TeriflunomideYield 71.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Ethyl 2-cyano-3-hydroxybut-2-enoate (III) (50 g) and 4-(trifluoromethyl) aniline (51.9 g) in xylene (1000 ml) was refluxed for 48 hours. The reaction mixture was allowed to cool at room temperature. Separated solid was filtered and washed with xylene (2×100 ml). Solid was dried under vacuum at 70° C. to yield (62 g) of Teriflunomide.

Workup

  1. customSeparated solid
  2. filtrationwas filtered
  3. washwashed with xylene (2×100 ml)
  4. customSolid was dried under vacuum at 70° C.

Sources & evidence

ORD record
ord-5e20d06d58c240d8b3aac1a708933418
Source dataset
uspto-grants-2013_03
Patent number
US08389757B2

Reaction notes

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