N-Methylaniline → HCID 19438634, compound

HRID 2225899Notes

Reaction equation

HRID 2225899 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.ClC[CH2:11][CH2:12][C:13]#[N:14].[C:15](=O)(O)[O-].[Na+]>>[C:13]([CH2:12][CH2:11][CH2:1][N:2]([CH3:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)#[N:14]

Participants

4

Reactant 3

HCID 7515N-MethylanilineHCID 123364-ChlorobutyronitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 19438634HCID 19438634, compound

Conditions

Temperature
110 °C

Procedure

To N-methylaniline (25 g) was added 4-chlorobutyronitrile (25 ml) and the mixture was stirred at 110° C. for 24 hours. After cooling, the mixture was neutralized with an aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was subjected to distillation under reduced pressure to obtain the desired compound (21.5 g) as pale yellow oil.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. distillationThe residue was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-fefaad9be0974a90b5a9c9d74582fa75
Source dataset
uspto-grants-1994_09
Patent number
US05344928

Reaction notes

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