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Acetyl chloride → N-acetyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(1-pyrazolyl)benzoic acid amide

HRID 1187952
ノート
印刷プレビュー

反応式

HRID 1187952 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:29]([F:32])([F:31])[F:30])[O:13][N:12]=[C:11]([C:14]3[CH:27]=[CH:26][C:17]([C:18]([NH:20][N:21]4[CH:25]=[CH:24][CH:23]=[N:22]4)=[O:19])=[C:16]([CH3:28])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[H-].[Na+].[H][H].[C:37](Cl)(=[O:39])[CH3:38]>O1CCCC1>[C:37]([N:20]([N:21]1[CH:25]=[CH:24][CH:23]=[N:22]1)[C:18](=[O:19])[C:17]1[CH:26]=[CH:27][C:14]([C:11]2[CH2:10][C:9]([C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)([C:29]([F:30])([F:32])[F:31])[O:13][N:12]=2)=[CH:15][C:16]=1[CH3:28])(=[O:39])[CH3:38]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 671639784-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(1-pyrazolyl)benzoic acid amideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 67164590N-acetyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(1-pyrazolyl)benzoic acid amide収率 26.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

In a solution of 0.20 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(1-pyrazolyl)benzoic acid amide in 3 mL of tetrahydrofuran, 0.027 g of 60% oily sodium hydride was added and stirred at room temperature for 10 minutes. After ceasing the generation of hydrogen gas, 0.049 g of acetyl chloride was added under cooling with ice and with stirring, and continued to stir at the same temperature further for 10 minutes. After the completion of the reaction, the reaction mixture was poured in 10 mL of ice water, extracted with ethyl acetate (10 mL×1), the organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (2:3) to obtain 0.058 g of the aimed product as yellow resinous substance.

後処理

  1. additionwas added
  2. temperatureunder cooling with ice
  3. stirringwith stirring
  4. stirringto stir at the same temperature further for 10 minutes
  5. customAfter the completion of the reaction
  6. extractionextracted with ethyl acetate (10 mL×1)
  7. dry with materialdried over saturated sodium chloride aqueous solution
  8. distillationanhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure
  9. customThe residue was purified with silica gel column chromatography that

出典と根拠

ORDレコード
ord-59540bc95f08413a8cd099ee5f4489b0
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08673951B2

反応ノート

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