Carbon Tetrachloride → 2-(Pyridin-4-yl)-6-(trifluoromethyl)benzo[d]oxazole

HRID 884836Notes

Reaction equation

HRID 884836 reaction equation
O[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.C(Cl)(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>O>[N:17]1[CH:16]=[CH:15][C:14]([C:13]2[O:20][C:2]3[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=3[N:12]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66881414N-(2-hydroxy-4-trifluoromethylphenyl)isonicotinamide

Product 1

HCID 668807592-(Pyridin-4-yl)-6-(trifluoromethyl)benzo[d]oxazoleYield 33.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.8 g of N-(2-hydroxy-4-trifluoromethylphenyl)isonicotinamide, 15 ml of carbon tetrachloride, 2.23 g of triphenylphosphine and 0.86 g of triethylamine was heated to reflux for five hours. The mixture was cooled to room temperature. Then, water was poured into the mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.25 g of 2-(pyridin-4-yl)-6-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 15”).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for five hours
  3. extractionfollowed by extraction with ethyl acetate twice
  4. washThe combined organic layers were washed with water
  5. dry with materiala saturated sodium chloride solution, dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c9eccdb355a34abfb4a24baeb32399c0
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Reaction notes

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