Toluene → 2-(4-Iodophenyl)benzoxazole

HRID 1028864Notes

Reaction equation

HRID 1028864 reaction equation
[I:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=O)=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[I:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]2[O:15][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 163509944-iodo-N-(2-hydroxyphenyl)benzamide

Product 1

HCID 28294142-(4-Iodophenyl)benzoxazoleYield 77.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

In a 300 mL three-neck flask were put 15 g (44 mmol) of 4-iodo-N-(2-hydroxyphenyl)benzamide and 24 g (0.14 mol) of para-toluenesulfonic acid monohydrate. The atmosphere in the flask was replaced with nitrogen. To this mixture was added 300 mL of toluene. The resulting mixture was stirred under a nitrogen stream at 110° C. for 4 hours. After that, this reaction mixture was added to about 300 mL of water, followed by extraction with ethyl acetate. Then, the organic layer and the extract were combined and washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine in that order. After that, magnesium sulfate was added to the organic layer to dry it. Next, this mixture was suction filtered through Celite. The resulting filtrate was concentrated to give a solid. This solid was recrystallized with a mixed solvent of ethyl acetate and hexane to give 11 g of a white solid in a yield of 75%.

Workup

  1. customIn a 300 mL three-neck flask were put
  2. extractionfollowed by extraction with ethyl acetate
  3. washwashed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine in that order
  4. additionAfter that, magnesium sulfate was added to the organic layer
  5. customto dry it
  6. filtrationfiltered through Celite
  7. concentrationThe resulting filtrate was concentrated
  8. customto give a solid
  9. customThis solid was recrystallized with a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-a523a196203843d196ef9db8b6f78f31
Source dataset
uspto-grants-2014_05
Patent number
US08735597B2

Reaction notes

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