Sodium Hydroxide → N-(3-Allyloxy-4-cyanophenyl)-2,2-dimethylpropionamide

HRID 501532Notes

Reaction equation

HRID 501532 reaction equation
[CH2:1]([O:4][C:5]1[CH:12]=[C:11]([NH2:13])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8])[CH:2]=[CH2:3].[OH-].[Na+].[C:16](Cl)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl>[CH2:1]([O:4][C:5]1[CH:12]=[C:11]([NH:13][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 62493Pivaloyl chlorideHCID 597542362-(Allyloxy)-4-aminobenzonitrile

Product 1

HCID 59754230N-(3-Allyloxy-4-cyanophenyl)-2,2-dimethylpropionamideYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 10B (1.9 g, 10.9 mmol) in anhydrous CH2Cl2 (16 mL) cooled at 0° C. was added 1 N aqueous NaOH solution (16.4 mL, 16.4 mmol), followed by pivaloyl chloride (1.9 mL, 15.3 mmol). After the addition, the reaction mixture was stirred at 0° C. for 2 h, then concentrated under reduced pressure to remove most of the CH2Cl2 solvent. The remaining residue was diluted with water, and the resulting precipitate collected by filtration, washed with water, hexane, and dried under vacuum to furnish the title compound as a light brown solid (2.6 g).

Workup

  1. additionAfter the addition
  2. concentrationconcentrated under reduced pressure
  3. customto remove most of the CH2Cl2 solvent
  4. additionThe remaining residue was diluted with water
  5. filtrationthe resulting precipitate collected by filtration
  6. washwashed with water, hexane
  7. customdried under vacuum

Sources & evidence

ORD record
ord-0be4df673f34498a9fada774b89f347a
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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