Triphenylphosphine → 2-(2-Methylsulfanylphenyl)-5-trifluoromethylbenzoxazole

HRID 923761Notes

Reaction equation

HRID 923761 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20][CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:21][S:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:13]1[O:22][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][C:3]=2[N:12]=1

Participants

5

Reactant 3

HCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 67981373N-(2-hydroxy-5-trifluoromethylphenyl)-2-methylsulfanylbenzamide

Product 1

HCID 679820782-(2-Methylsulfanylphenyl)-5-trifluoromethylbenzoxazoleYield 89.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N-(2-hydroxy-5-trifluoromethylphenyl)-2-methylsulfanylbenzamide (0.33 g), triphenylphosphine (0.34 g), and THF (7 ml), diethyl azodicarboxylate (40% in toluene) (0.57 g) was added dropwise, and stirred at room temperature for 1.5 hours. Triphenylphosphine (79 mg) and diethyl azodicarboxylate (40% in toluene. 0.13 g) were added to the mixture, and stirred for further 1 hour. The mixture was heated to 50° C., and stirred for 1.5 hours. The reaction mixture was cooled to room temperature, and then the mixture was allowed to stand at room temperature overnight. The reaction mixture was subjected to silica gel column chromatography to give 0.28 g of 2-(2-methylsulfanylphenyl)-5-trifluoromethylbenzoxazole (hereinafter referred to as Present Compound 77).

Workup

  1. additionwas added dropwise
  2. stirringstirred for further 1 hour
  3. temperatureThe mixture was heated to 50° C.
  4. stirringstirred for 1.5 hours
  5. temperatureThe reaction mixture was cooled to room temperature
  6. waitto stand at room temperature overnight

Sources & evidence

ORD record
ord-8672518611154f768479aecc2922cea9
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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