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

HRID 2378482Notes

Reaction equation

HRID 2378482 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 N-(4-chloro-2-methyl-3-trifluoromethylphenyl)-2,2-dimethylpropionamide (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 resulting solid was filtered, washed with water and dried to yield an 85:15 mixture (7.55 g) of compound 841C and 841D. The resulting mixture was used in the next step.

Workup

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

Sources & evidence

ORD record
ord-460631b3949345419295edf70ef8bb4d
Source dataset
uspto-grants-2008_12
Patent number
US07470797B2

Reaction notes

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