Iodo benzene diacetate → HCID 51346945, compound

HRID 2190714Notes

Reaction equation

HRID 2190714 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]([F:19])([F:18])[F: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]([F:18])([F:17])[F:19])=[CH:15][C:10]=2[N:9]=1

Participants

4

Reactant 2

HCID 12217721Iodo benzene diacetateHCID 136331267HCID 136331267, compound

Product 1

HCID 51346945HCID 51346945, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 0.71 g of 2-(3-chloropyridin-4-yl)methylideneamino-4-(trifluoromethyl)phenol and 10 ml of methanol, 0.80 g of iodobenzene diacetate was added at room temperature and stirred for 2.5 hours. The reaction mixture was concentrated under reduced pressure, and then water was added to the reaction mixture, followed by extraction with ethyl acetate. Organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.14 g of 2-(3-chloropyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 18”).

Workup

  1. additionwas added at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionwater was added to the reaction mixture
  4. extractionfollowed by extraction with ethyl acetate
  5. washOrganic layers were washed with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f22b86af90344c31b9e4568ca1af5ef8
Source dataset
uspto-grants-2012_12
Patent number
US08324387B2

Reaction notes

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