Sodium hydride → [3-(4-Trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-on-4-yl]methyl 4-trifluoromethylbenzoate

HRID 1880703노트

반응식

HRID 1880703 반응식
[H-].[Na+].[F:3][C:4]([F:18])([F:17])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[NH:12][O:13][C:14](=[O:16])[N:15]=2)[CH:6]=1.[F:19][C:20]([F:33])([F:32])[C:21]1[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28]Cl)=[O:26])=[CH:23][CH:22]=1.[Cl-].[NH4+]>CN(C)C=O>[F:19][C:20]([F:32])([F:33])[C:21]1[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][N:15]2[C:14](=[O:16])[O:13][N:12]=[C:11]2[C:7]2[CH:6]=[C:5]([C:4]([F:3])([F:17])[F:18])[CH:10]=[CH:9][N:8]=2)=[O:26])=[CH:23][CH:22]=1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59570348Chloromethyl 4-trifluoromethylbenzoateHCID 178517507HCID 178517507, 화합물

생성물 1

HCID 59570284[3-(4-Trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-on-4-yl]methyl 4-trifluoromethylbenzoate수율 17.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Into 2 ml of N,N-dimethylformamide was suspended 0.07 g of sodium hydride (60% oily), and 0.3 g of 3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one was added at room temperature. After stirring for 15 minutes, 0.33 g of chloromethyl 4-trifluoromethylbenzoate was added, and the mixture was stirred at 70° C. for 4 hours. The reaction solution was allowed to cool to room temperature, and poured into an aqueous saturated ammonium chloride solution, followed by extraction with ethyl acetate three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.1 g of [3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-on-4-yl]methyl 4-trifluoromethylbenzoate (present compound (43)).

후처리

  1. additionwas added at room temperature
  2. stirringthe mixture was stirred at 70° C. for 4 hours
  3. extractionfollowed by extraction with ethyl acetate three times
  4. washwashed with an aqueous saturated sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4bd8ce6472604aa79609b759d98b2abe
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318776B2

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