Hydrogen Peroxide → N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-3-nitro-2,4,5-trifluoro-benzamide

HRID 1943119ノート

反応式

HRID 1943119 の反応式
[NH2:1][C:2]1[C:3]([F:31])=[C:4]([CH:26]=[C:27]([F:30])[C:28]=1[F:29])[C:5]([NH:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([C:15]([F:24])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:10][C:9]=1[CH3:25])=[O:6].FC(F)(F)C(O)=[O:35].OO.[OH2:41]>C(Cl)(Cl)Cl>[CH3:25][C:9]1[CH:10]=[C:11]([C:15]([F:24])([C:20]([F:21])([F:22])[F:23])[C:16]([F:18])([F:19])[F:17])[CH:12]=[C:13]([CH3:14])[C:8]=1[NH:7][C:5](=[O:6])[C:4]1[CH:26]=[C:27]([F:30])[C:28]([F:29])=[C:2]([N+:1]([O-:35])=[O:41])[C:3]=1[F:31]

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 6422Trifluoroacetic acidHCID 592269383-amino-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2,4,5-trifluoro-benzamide

生成物 1

HCID 59226973N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-3-nitro-2,4,5-trifluoro-benzamide収率 68.5%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
55 °C

実験手順

To a solution of 3-amino-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2,4,5-trifluoro-benzamide (32.8 g, 71 mmol) (Example I14) and trifluoro-acetic acid (237 ml) in chloroform (118 ml) was added drop-wise aqueous hydrogen peroxide (67 ml) (35% w/v). The reaction mixture was kept at approximately 50° C. with external cooling. The reaction mixture was stirred at 55° C. for 30 minutes, then poured onto a mixture of ice and water. The mixture was extracted twice with dichloromethane. The combined organic phases were washed with aqueous sodium hydrogen carbonate (1M), dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 7:3) to give N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-3-nitro-2,4,5-trifluoro-benzamide (23.94 g, 68.5% yield). 1H-NMR (400 MHz, CDCl3): 2.35 (6H, s), 7.38 (2H, s), 7.68 (1H, d), 8.25 (1H, m) ppm.

後処理

  1. customwas kept at approximately 50° C. with external cooling
  2. extractionThe mixture was extracted twice with dichloromethane
  3. washThe combined organic phases were washed with aqueous sodium hydrogen carbonate (1M)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 7:3)

出典と根拠

ORDレコード
ord-8991518d60054a83b632a678b8006d4e
出典データセット
uspto-grants-2013_03
特許番号
US08389766B2

反応ノート

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