2-(2-Dimethylamino-ethoxy)-benzoic acid → 5-{2-[2-(N,N-dimethylamino)ethyl]oxy-phenyl}-3-(4-hydroxy-phenyl)-1,2,4-oxadiazole

HRID 650990Notes

Reaction equation

HRID 650990 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=O)[CH3:3].Cl.[NH:17]=[C:18]=[NH:19].[OH:20][C:21]1[C:29]2N=NN[C:25]=2[CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[CH3:3][N:2]([CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]1[O:11][N:19]=[C:18]([C:24]2[CH:25]=[CH:29][C:21]([OH:20])=[CH:22][CH:23]=2)[N:17]=1)[CH3:1]

Participants

5

Reactant 3

HCID 64846592-(2-Dimethylamino-ethoxy)-benzoic acidHCID 21863233HCID 21863233, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 1357040725-{2-[2-(N,N-dimethylamino)ethyl]oxy-phenyl}-3-(4-hydroxy-phenyl)-1,2,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,45 g of 2-[2-(N,N-dimethylamino)ethyl]oxy-benzoic acid are dissolved with 1.91 g of N-ethyl-N-dimethylaminopropyl)carbodiimide hydrochloride and catalytic amounts of hydroxybenzotriazole in 50 ml of DMF. After 15 minutes 1.52 g of 4-hydroxybenzoic acid amidoxime are added and the mixture is heated for 15 minutes at 700 W in the microwave. It is concentrated by evaporation, the residue is taken up in ethyl acetate, washed with water, dried over sodium sulphate and concentrated by evaporation in vacuo. The residue is filtered over silica gel with ethanol and converted into the salt as described above. Yield: 1.1 g (29% of theory). m.p.: 170° C. (decomposition).

Workup

  1. temperaturethe mixture is heated for 15 minutes at 700 W in the microwave
  2. concentrationIt is concentrated by evaporation
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation in vacuo
  6. filtrationThe residue is filtered over silica gel with ethanol

Sources & evidence

ORD record
ord-395f7e2733714ed5a0676bfde1abe881
Source dataset
uspto-grants-2001_08
Patent number
US06277872B1

Reaction notes

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