Potassium Carbonate → 2-[4-(6-chlorobenzoxazol-2-yloxy)phenoxy]propionic acid N-cyano-N-butylamide

HRID 845694Notes

Reaction equation

HRID 845694 reaction equation
[C:1]([N:3]([CH2:16][CH2:17][CH2:18][CH3:19])[C:4](=[O:15])[CH:5]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1O)[CH3:6])#[N:2].Cl[C:21]1[O:22][C:23]2[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:24]=2[N:25]=1.C(=O)([O-])[O-:32].[K+].[K+]>C(#N)C>[C:1]([N:3]([CH2:16][CH2:17][CH2:18][CH3:19])[C:4](=[O:15])[CH:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:32][C:21]2[O:22][C:23]3[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:24]=3[N:25]=2)=[CH:10][CH:9]=1)[CH3:6])#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 771752,6-DichlorobenzoxazoleHCID 538549152-(hydroxyphenoxy)propionic acid N-cyano-N-butylamide

Product 1

HCID 544438442-[4-(6-chlorobenzoxazol-2-yloxy)phenoxy]propionic acid N-cyano-N-butylamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.4 g (0.017 mole) of 2-(hydroxyphenoxy)propionic acid N-cyano-N-butylamide, 3.8 g (0.02 mole) of 2,6-dichlorobenzoxazole and 3.5 g (0.025 mole) of potassium carbonate are stirred in 50 ml of acetonitrile for 10 hours at room temperature. The salts are then removed by filtration and the filtrate is concentrated by evaporation. The residue is chromatographed through silica gel eluted with ethyl acetate/hexane (1:3), affording 2-[4-(6-chlorobenzoxazol-2-yloxy)phenoxy]propionic acid N-cyano-N-butylamide with a melting point of 91°-92° C.

Workup

  1. customThe salts are then removed by filtration
  2. concentrationthe filtrate is concentrated by evaporation
  3. customThe residue is chromatographed through silica gel
  4. washeluted with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-f033b832923c42d48923f03759ed7dc7
Source dataset
uspto-grants-1988_07
Patent number
US04759796

Reaction notes

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