Acetic Acid → HCID 22555951, compound

HRID 2358291Notes

Reaction equation

HRID 2358291 reaction equation
[OH:1][C:2]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[C:4](=[O:13])N1C1C=CC=CC=1.C(O)(=[O:28])C>Cl.O1CCOCC1>[OH:28][C:2]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[C:4](=[O:13])[O:1]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 22555997HCID 22555997, compound

Product 1

HCID 22555951HCID 22555951, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2 (3.11 g, 9.39 mmol) in a mixture of 6N hydrochloric acid (150 mL) and dioxane (150 mL) was heated at reflux under Ar for 18 h. Acetic acid (50 mL) was added and heating was continued for an additional 4 h. The organic solvents were removed in vacuo and the remaining aqueous was extracted with ethyl acetate (3×), washed with brine and dried with sodium sulfate (anh.). Filtration followed by removal of the solvent in vacuo gave 3 as a white solid (1.32 g, 55%)

Workup

  1. temperaturewas heated
  2. temperatureat reflux under Ar for 18 h
  3. temperatureheating
  4. customThe organic solvents were removed in vacuo
  5. extractionthe remaining aqueous was extracted with ethyl acetate (3×)
  6. washwashed with brine
  7. dry with materialdried with sodium sulfate (anh.)
  8. filtrationFiltration
  9. customfollowed by removal of the solvent in vacuo

Sources & evidence

ORD record
ord-f5774116bf5d4c3591d5a2f5ee4c2f1e
Source dataset
uspto-grants-2010_07
Patent number
US07763614B2

Reaction notes

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