Iodo benzene diacetate → HCID 51346945, compound

HRID 1913604Notes

Reaction equation

HRID 1913604 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-9a11bb6c9631467ebf251fe89074f839
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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