N-Methylaniline → HCID 19438634, compound

HRID 1733863Notes

Reaction equation

HRID 1733863 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-2b6770a06c2942b09506b119eba9d2c6
Source dataset
uspto-grants-1996_07
Patent number
US05532171

Reaction notes

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