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

HRID 923761노트

반응식

HRID 923761 반응식
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

참가 물질

5

반응물 3

HCID 11776Triphenylphosphine2회HCID 220568ethyl N-ethoxycarbonyliminocarbamate2회HCID 67981373N-(2-hydroxy-5-trifluoromethylphenyl)-2-methylsulfanylbenzamide

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8672518611154f768479aecc2922cea9
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278983B2

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