Iodo benzene diacetate → HCID 58148285, compound

HRID 2190716Notes

Reaction equation

HRID 2190716 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=[N:9][C:10]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[CH:12][C:11]=1[OH:20].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CO>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:20][C:11]2[CH:12]=[CH:13][C:14]([C:16]([CH3:17])([CH3:19])[CH3:18])=[CH:15][C:10]=2[N:9]=1

Participants

4

Reactant 2

HCID 12217721Iodo benzene diacetateHCID 136184230HCID 136184230, compound

Product 1

HCID 58148285HCID 58148285, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 0.49 g of 2-(3-chloropyridin-4-yl)methylideneamino-4-tert-butylphenol and 10 ml of methanol, 0.57 g of iodobenzene diacetate was added at room temperature and stirred for two hours. The reaction mixture was concentrated, and then water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated sodium chloride solution sequentially, and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.21 g of 2-(3-chloropyridin-4-yl)-5-tert-butylbenzoxazole (hereinafter, referred to as “active compound 20”).

Workup

  1. additionwas added at room temperature
  2. concentrationThe reaction mixture was concentrated
  3. additionwater was added
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  6. dry with materiala saturated sodium chloride solution sequentially, and dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f9b6478df824aadb7d3f591c9851e76
Source dataset
uspto-grants-2012_12
Patent number
US08324387B2

Reaction notes

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