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

HRID 1880703ノート

反応式

HRID 1880703 の反応式
[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

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59570348Chloromethyl 4-trifluoromethylbenzoateHCID 178517507HCID 178517507、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)).

後処理

  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

出典と根拠

ORDレコード
ord-4bd8ce6472604aa79609b759d98b2abe
出典データセット
uspto-grants-2012_11
特許番号
US08318776B2

反応ノート

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