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Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → 4-[5-(3,5-Dichloro-phenyl)-2,5-dimethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-benzamide

HRID 405698
ノート
印刷プレビュー

反応式

HRID 405698 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24](F)(F)F)[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.F[B-](F)(F)F.[CH3:33][O+](C)C>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH3:24])[O:13][N:12]([CH3:33])[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[C:16]([CH3:23])[CH:15]=3)=[CH:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)3 回HCID 667845734-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide

生成物 1

HCID 892620034-[5-(3,5-Dichloro-phenyl)-2,5-dimethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-benzamide収率 29.9%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a solution of 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzamide (200 mg) in 1,2-dichloroethane (3 ml) was added trimethyloxonium tetrafluoroborate (85 mg) and the reaction mixture was stirred at room temperature for 19 hours then more trimethyloxonium tetrafluoroborate (210 mg). After 4 hours 30 minutes, more trimethyloxonium tetrafluoroborate (0.5 ml) was added and after 2 hours, the reaction mixture was heated at (85° C.) for 18 hours. The solution was then concentrated under vacuo to give a crude residue (210 mg). Part of this residue (100 mg) of the crude was extracted between AcOEt and saturated NaHCO3. The organic phases were gathered, dried over anhydrous MgSO4, filtered and evaporated to give the desired compound (54 mg). 1H-NMR (CDCl3, δ in ppm): 7.50-7.31 (m, 6H), 5.75 (bs, 2H), 5.41 (s, 1H), 2.99 (s, 3H), 2.52 (s, 3H).

後処理

  1. temperaturethe reaction mixture was heated at (85° C.) for 18 hours
  2. concentrationThe solution was then concentrated under vacuo
  3. customto give a crude residue (210 mg)
  4. extractionPart of this residue (100 mg) of the crude was extracted between AcOEt and saturated NaHCO3
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-b7ac525a66e94810aea5a48371e3663e
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08754053B2

反応ノート

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