Phenol → HCID 12678053, compound

HRID 1591802Notes

Reaction equation

HRID 1591802 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Cl:10][C:11]1[C:20](Cl)=[N:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1>C1COCC1>[Cl:10][C:11]1[C:20]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 166592,3-DichloroquinoxalineHCID 24758Sodium hydride

Product 1

HCID 12678053HCID 12678053, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of phenol (564 mg, 6 mmol) in THF (5 ml) was added to a suspension of sodium hydride (60% in mineral oil, 240 mg, 6 mmol) in THF (10 ml). After 10 min 2,3-dichloroquinoxaline (995 mg, 5 mmol) was added. The mixture was stirred for 3 days. The solvent was removed in vacuo, the residue was dissolved in EtOAc, washed with NaOH (1M), dried (Na2SO4) and evaporated in vacuo to give a yellow solid. Recrystallisation from diisopropylether gave the title compound as off-white needles: δH (DMSO d6) 8.01-7.98 (1H, m), 7.77-7.67 (3H, m), 7.53-7.48 (2H, m), 7.37-7.30 (3H, m); m/z (EI+, 70V) 257.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with NaOH (1M)
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customto give a yellow solid
  7. customRecrystallisation from diisopropylether

Sources & evidence

ORD record
ord-6d8e6d20c44e4cf7ab704ffbec801f9a
Source dataset
uspto-grants-2007_11
Patent number
US07291645B2

Reaction notes

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