Acetonitrile → HCID 28584403, compound

HRID 1493614Notes

Reaction equation

HRID 1493614 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])[CH3:2].C(=O)(O)[O-].[Na+].Cl[CH2:16][C:17]([O:19][CH3:20])=[O:18].C(#N)C>CCOCC>[CH2:1]([C:3]1[CH:4]=[C:5]([NH:6][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7295Methyl chloroacetateHCID 114753-EthylanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 28584403HCID 28584403, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To m-ethylaniline (50 g; 0.413 mol) and sodium bicarbonate (69.33 g; 0.825 mol) was added methyl chloroacetate (39.79 ml; 0.454 mol) and acetonitrile (50 ml). The mixture was allowed to heat to 130° with stirring from 48 hours. The mixture was then taken up in ether. The ether extract was treated with 2N hydrochloric acid, after which the acid layer was extracted with ether. The combined organic extracts were washed with water, brine and then dried (Na2SO4). Filtration and evaporation of the solvent gave the title compound (36.95 g: 46%) as an oil.

Workup

  1. temperatureto heat to 130°
  2. extractionThe ether extract
  3. additionwas treated with 2N hydrochloric acid
  4. extractionafter which the acid layer was extracted with ether
  5. washThe combined organic extracts were washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-ed159a46b73242a3bf720997916042f3
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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