Tetrahydrofuran → HCID 57440914, compound

HRID 1353654Notes

Reaction equation

HRID 1353654 reaction equation
C1(C([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:12][C:11]=2[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])=O)C=CC=CC=1.O1CCCC1>CO.[OH-].[Na+]>[C:26]1([C:24]([C:11]2[CH:12]=[C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:14]=[CH:15][C:10]=2[NH2:9])=[O:25])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 85806873HCID 85806873, compound

Product 1

HCID 57440914HCID 57440914, compoundYield 107.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of phenyl-N-[2-(phenylcarbonyl)-4-(phenylmethoxy)phenyl]carboxamide (3.24 g, 8.0 mmol) in methanol (20 mL) and 10 N sodium hydroxide (NaOH) (6 mL) was heated to reflux temperature when tetrahydrofuran (THF) (15 mL) was added. The solution was then heated to reflux overnight when the methanol and THF was removed under vacuo. The solution was then added to water (100 mL) and extracted with ethyl acetate (3×40 mL). The combined organic layers were dried (Na2SO4) and concentrated under vacuo to an oil to isolate the title compound (2.60 g, >100% yield, analytical).

Workup

  1. additionwas added
  2. temperatureThe solution was then heated
  3. customwas removed under vacuo
  4. additionThe solution was then added to water (100 mL)
  5. extractionextracted with ethyl acetate (3×40 mL)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated under vacuo to an oil

Sources & evidence

ORD record
ord-ff8f6b65f85a4a419a6103332949c035
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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