Potassium Carbonate → alpha-(3-(4-(2-Quinolinylmethyloxy)phenoxymethyl)phenoxy)acetonitrile

HRID 2074025Notes

Reaction equation

HRID 2074025 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[O:6][CH2:7][C:8]#[N:9].[N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[CH2:23][O:24][C:25]1[CH:31]=[CH:30][C:28]([O-:29])=[CH:27][CH:26]=1.[Na+].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[CH2:23][O:24][C:25]1[CH:31]=[CH:30][C:28]([O:29][CH2:2][C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=2)[O:6][CH2:7][C:8]#[N:9])=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 14774148alpha-(3-Chloromethylphenoxy)acetonitrileHCID 23684421Sodium 4-(2-quinolinylmethyloxy)phenoxide

Product 1

HCID 14774149alpha-(3-(4-(2-Quinolinylmethyloxy)phenoxymethyl)phenoxy)acetonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of α-(3-chloromethylphenoxy)acetonitrile (0.025 mol), sodium 4-(2-quinolinylmethyloxy)phenoxide (0.025 mol) and anhydrous potassium carbonate (0.125 mol) in dimethylsulfoxide (50 ml) is stirred at ambient temperature for 18 hrs. The reaction is diluted with water (600 ml) and extracted with ethylacetate (3×150 ml). The ethyl acetate solution is washed with water (3×100 ml) and brine (100 ml) then dried and evaporated to give α-(3-(4-(2-quinolinylmethyloxy)phenoxymethyl)phenoxy)acetonitrile. (M.P. 110°-114° C.)

Workup

  1. extractionextracted with ethylacetate (3×150 ml)
  2. washThe ethyl acetate solution is washed with water (3×100 ml) and brine (100 ml)
  3. customthen dried
  4. customevaporated

Sources & evidence

ORD record
ord-80cbdb1bf2af4ab8976b7c0f718834f4
Source dataset
uspto-grants-1990_04
Patent number
US04920132

Reaction notes

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