Ethyl Acetate → HCID 57663162, compound

HRID 548724Notes

Reaction equation

HRID 548724 reaction equation
[C:1]1(C)[CH:6]=CC(S([O-])(=O)=O)=C[CH:2]=1.[NH+]1C=CC=CC=1.[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH2:25])=[O:24])=[C:21]([OH:28])[CH:20]=1.C(OCC)(=O)C>COC(OC)(C)C>[F:18][C:19]1[CH:27]=[CH:26][C:22]2[C:23](=[O:24])[NH:25][C:1]([CH3:6])([CH3:2])[O:28][C:21]=2[CH:20]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 225633144-Fluoro-2-hydroxybenzamide

Product 1

HCID 57663162HCID 57663162, compoundYield 701.1%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Conditions

Temperature
83 °C

Procedure

Pyridinium toluene-4-sulfonate (49 mg, 0.19 mmol) was added to a mixture of 4-fluoro-2-hydroxybenzamide (0.3 g, 1.93 mmol) in 2,2-dimethoxypropane (5 mL) and heated at 83° C. for 20 hours. The reaction mixture was reduced in vacuo and ethyl acetate (30 mL) added. The mixture was washed with 10% potassium carbonate solution (2×20 mL), brine (20 mL), dried (MgSO4), and reduced in vacuo to give a white solid. The material was chromatographed on silica, eluting with 40-70% ethyl acetate in isohexane, to give the desired compound as a white solid (0.26 g).

Workup

  1. additionadded
  2. washThe mixture was washed with 10% potassium carbonate solution (2×20 mL), brine (20 mL)
  3. dry with materialdried (MgSO4)
  4. customto give a white solid
  5. customThe material was chromatographed on silica
  6. washeluting with 40-70% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-14461e115b8a46ce9c3aa30ccefbfc5a
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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