Hydrochloric Acid → Teriflunomide

HRID 1967640Notes

Reaction equation

HRID 1967640 reaction equation
Br[CH:2]([C:16](=[O:18])[CH3:17])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)=[O:4].[C-:19]#[N:20].[Na+].Cl>CS(C)=O.O>[CH3:17]/[C:16](/[OH:18])=[C:2](/[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)=[O:4])\[C:19]#[N:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 446287412-Bromo-3-oxo-N-(4-(trifluoromethyl)phenyl)butanamide

Product 1

HCID 54684141TeriflunomideYield 85.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 2-bromo-3-oxo-N-[4-(trifluoromethyl)phenyl]butanamide (10 g) [obtained from above step-b] and sodium cyanide (1.69 g) in DMSO (30 ml) was stirred at room temperature overnight. The reaction mixture was diluted with water (100 ml) and acidified with 50% HCl solution. Precipitated solid was filtered and washed with water. The solid was dried to give Teriflunomide (7.12 g).

Workup

  1. customPrecipitated solid
  2. filtrationwas filtered
  3. washwashed with water
  4. customThe solid was dried

Sources & evidence

ORD record
ord-55d865392aa344809251822d20f8c464
Source dataset
uspto-grants-2013_04
Patent number
US08420856B2

Reaction notes

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