2,5-Diphenyloxazole → 2,5-Diphenyl-3-methyloxazolium Toluenesulfonate

HRID 1248097Notes

Reaction equation

HRID 1248097 reaction equation
[C:1]1([C:7]2[O:8][C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]1([CH3:29])[C:19]([S:24]([O:27]C)(=[O:26])=[O:25])=[CH:20][CH:21]=[CH:22][CH:23]=1>CCOCC>[C:18]1([CH3:29])[C:19]([S:24]([O-:27])(=[O:26])=[O:25])=[CH:20][CH:21]=[CH:22][CH:23]=1.[C:1]1([C:7]2[O:8][C:9]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:10][N+:11]=2[CH3:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 71052,5-DiphenyloxazoleHCID 90076Benzenesulfonic acid, 2-methyl-, methyl ester

Product 1

HCID 867401402,5-Diphenyl-3-methyloxazolium ToluenesulfonateYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

10 g of 2,5-Diphenyloxazole was heated at 125° C. for 5-10 minutes with 30 g of methyl toluenesulfonate, both commercially available compounds. The solution was cooled, and anhydrous ether was added to precipitate the product. The product was recrystallized by dissolving in absolute ethanol and then adding ethyl acetate. The product was obtained in 95% yield, and had a melting point of 167°-168° C.

Workup

  1. temperatureThe solution was cooled
  2. customto precipitate the product
  3. customThe product was recrystallized
  4. dissolutionby dissolving in absolute ethanol
  5. customThe product was obtained in 95% yield

Sources & evidence

ORD record
ord-49322eb33abf4007ba34e4762fa4bbb1
Source dataset
uspto-grants-1985_06
Patent number
US04522742

Reaction notes

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