Sodium Carbonate → N,N-diethyl-(2-phenyl-4-quinazolinyl)oxyacetamide

HRID 2232564Notes

Reaction equation

HRID 2232564 reaction equation
[C:1]1([C:7]2[N:16]=[C:15]([OH:17])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:18]([N:20]([CH2:25][CH3:26])[C:21](=[O:24])[CH2:22]Cl)[CH3:19].C(=O)([O-])[O-].[Na+].[Na+]>CC(=O)CC>[CH2:18]([N:20]([CH2:25][CH3:26])[C:21](=[O:24])[CH2:22][O:17][C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:16]=1)[CH3:19]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 16844Chloro-N,N-diethylacetamideHCID 178517457HCID 178517457, compound

Product 1

HCID 13769197N,N-diethyl-(2-phenyl-4-quinazolinyl)oxyacetamideYield 59.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2-phenyl-4-quinazolinol (4.45 g), N,N-diethylchloroacetamide (3.3 g), sodium carbonate (4.25 g) and cuprous iodide (1 g) in 2-butanone (70 cc) is brought to boiling for 22 hours. The solvent is evaporated off under reduced pressure, water (100 cc) is added, the mixture is alkalinised with ammonia solution and the aqueous phase is extracted with methylene chloride (3×100 cc). The organic phase is dried over magnesium sulphate and evaporated to dryness under reduced pressure. The residue is chromatographed on silica gel with a cyclohexane/ethyl acetate (1:1 by volume) mixture as eluant. After crystatllization in isopropyl ether, N,N-diethyl-(2-phenyl-4-quinazolinyl)oxyacetamide (4 g), m.p. 113° C., is obtained.

Workup

  1. customThe solvent is evaporated off under reduced pressure, water (100 cc)
  2. additionis added
  3. extractionthe aqueous phase is extracted with methylene chloride (3×100 cc)
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. customevaporated to dryness under reduced pressure
  6. customThe residue is chromatographed on silica gel with a cyclohexane/ethyl acetate (1:1 by volume) mixture as eluant

Sources & evidence

ORD record
ord-aef656cfc6b541bfb62831257364dc99
Source dataset
uspto-grants-1988_11
Patent number
US04788204

Reaction notes

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