N-[4-chloro-2-methyl-3-(trifluoromethyl)phenyl]-2,2-dimethylpropanamide → N-(4-cyano-2-methyl-3-(trifluoromethyl)phenyl)pivalamide

HRID 501553Notes

Reaction equation

HRID 501553 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([CH3:15])[C:3]=1[C:16]([F:19])([F:18])[F:17].[C:20]([Cu])#[N:21]>CN1CCCC1=O>[C:20]([C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([CH3:15])[C:3]=1[C:16]([F:19])([F:18])[F:17])#[N:21]

Participants

4

Reactant 2

HCID 21874848N-[4-chloro-2-methyl-3-(trifluoromethyl)phenyl]-2,2-dimethylpropanamideHCID 178418546HCID 178418546, compound

Product 1

HCID 21875020N-(4-cyano-2-methyl-3-(trifluoromethyl)phenyl)pivalamideYield 93.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A suspension of compound 18B (8.36 g, 28.5 mmol) and CuCN (4.33 g, 65.5 mmol) in anhydrous N-methylpyrrolidinone (85 mL) was refluxed for 38 h. After cooling to rt, the suspension was poured into ice/water with stirring. The solid was filtered, washed with water and dried to yield an 85:15 mixture (7.55 g) of compounds 18C and 18D.

Workup

  1. temperaturewas refluxed for 38 h
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-02f00ddbe2034e76b483b6aa5fdc06e4
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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