Water → HCID 15086620, compound

HRID 359093Notes

Reaction equation

HRID 359093 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].Cl[CH2:29][C:30]#[N:31].O>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=2)[CH2:29][C:30]#[N:31])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7856ChloroacetonitrileHCID 516892Sodium BicarbonateHCID 14882805HCID 14882805, compound

Product 1

HCID 15086620HCID 15086620, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 4-[3-[N-(4-chlorophenyl)amino]propoxy]benzoate (1.2 g) was dissolved in DMF (10 ml), and under heating with stirring at 90° C., sodium bicarbonate (7.6 g) and chloroacetonitrile (6.63 g) were added thereto in 8-10 portions respectively over a period of 7 days. The reaction mixture was cooled, and water and ethyl acetate were added thereto and the mixture was separated into layers. The organic layer was washed with aqueous sodium chloride solution, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with chloroform to give the oily desired product (1.00 g).

Workup

  1. temperatureunder heating
  2. temperatureThe reaction mixture was cooled
  3. customthe mixture was separated into layers
  4. washThe organic layer was washed with aqueous sodium chloride solution
  5. concentrationconcentrated under reduced pressure
  6. washeluted with chloroform

Sources & evidence

ORD record
ord-1faef08dbfcb49e7876c2d9419e6f105
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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