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

HRID 2110500Notes

Reaction equation

HRID 2110500 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-180b793c95c64cfda36d4ed84a73f11f
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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