Phenol → 1-(4-Chlorophenyl)-1,2-dihydro-3-phenoxyquinoxalin-2-one

HRID 848476Notes

Reaction equation

HRID 848476 reaction equation
[H-].[Na+].C1OCCOCCOCCOCCOC1.[C:18]1([OH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl[C:26]1[C:27](=[O:43])[N:28]([C:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=2)[C:29]2[C:34]([N:35]=1)=[CH:33][CH:32]=[CH:31][CH:30]=2>C1(C)C=CC=CC=1.O>[Cl:42][C:39]1[CH:38]=[CH:37][C:36]([N:28]2[C:29]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:35]=[C:26]([O:24][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:27]2=[O:43])=[CH:41][CH:40]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 24758Sodium hydrideHCID 3633615-Crown-52×HCID 205654663-Chloro-1-(4-chlorophenyl)-1,2-dihydroquinoxalin-2-one

Product 1

HCID 205654801-(4-Chlorophenyl)-1,2-dihydro-3-phenoxyquinoxalin-2-oneYield 62.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A mixture of sodium hydride (0.65 g), "15-crown-5" (1,4,7,10,13-pentaoxacyclopentadecane) (0.5 ml), phenol (2.2 g), and dry toluene was stirred for 30 minutes. To this was added a suspension of 3-chloro-1-(4-chlorophenyl)-1,2-dihydroquinoxalin-2-one (6.0 g) in dry toluene (30 ml) and stirring was continued for 2 hours. Water was added and the product was extracted into chloroform. Evaporation of the solvent and crystallisation from ethanol gave the title compound (4.5 g) mp 239°-241° C.

Workup

  1. additionTo this was added
  2. stirringstirring
  3. waitwas continued for 2 hours
  4. extractionthe product was extracted into chloroform
  5. customEvaporation of the solvent and crystallisation from ethanol

Sources & evidence

ORD record
ord-d33363d7642f40b2a42e9ffcbcdd1721
Source dataset
uspto-grants-1981_10
Patent number
US04296114

Reaction notes

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