Water → HCID 57748865, compound

HRID 598524Notes

Reaction equation

HRID 598524 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10](O)[CH:9]=[N:8]2)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:18])=O.O>C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([Cl:18])[CH:9]=[N:8]2)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 178440679HCID 178440679, compound

Product 1

HCID 57748865HCID 57748865, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 250 mg (1.236 mmol) of 6-tert-Butyl-quinoxalin-2-ol in 1.07 mL (11.43 mmol) phosphorus oxychloride under nitrogen was heated at 110° C. for 3 h. The solution was cooled to room temperature and added drop wise to water (10-15° C.). Ethyl acetate was added. The aqueous layer was extracted with ethylacetate. The combined organic phases were washed with water, dried over Na2SO4 and concentrated. The crude compound was purified with flash column chromatography on silica eluting with a gradient formed from n-heptane and ethyl acetate to provide 219 mg (80.3%) of the title compound as a green solid. MS(m/e): 220 (M+H+).

Workup

  1. extractionThe aqueous layer was extracted with ethylacetate
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude compound was purified with flash column chromatography on silica eluting with a gradient
  6. customformed from n-heptane and ethyl acetate

Sources & evidence

ORD record
ord-123d060285ba4e2996a242187ccf78c6
Source dataset
uspto-grants-2011_03
Patent number
US07897627B2

Reaction notes

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