Hydrochloric Acid → N-[3,5-bis(trifluoromethyl)phenyl]-2,4-dioxobicyclo[3.2.1]octane-3-carboxamide

HRID 349789ノート

反応式

HRID 349789 の反応式
[CH:1]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[O:9])[CH2:3][C:2]2=[O:10].[F:11][C:12]([F:27])([F:26])[C:13]1[CH:14]=[C:15]([N:23]=[C:24]=[O:25])[CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1.[H-].[Na+].Cl>CN(C)C=O.O>[F:11][C:12]([F:26])([F:27])[C:13]1[CH:14]=[C:15]([NH:23][C:24]([CH:3]2[C:4](=[O:9])[CH:5]3[CH2:8][CH:1]([CH2:7][CH2:6]3)[C:2]2=[O:10])=[O:25])[CH:16]=[C:17]([C:19]([F:22])([F:20])[F:21])[CH:18]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 144686Bicyclo(3.2.1)octane-2,4-dioneHCID 27333143,5-Bis(trifluoromethyl)phenyl isocyanate

生成物 1

HCID 11603558N-[3,5-bis(trifluoromethyl)phenyl]-2,4-dioxobicyclo[3.2.1]octane-3-carboxamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of bicyclo[3,2,1]octane-2,4-dione (0.34 g, 2.5 mmole), 3,5-bis(trifluoromethyl)phenyl isocyanate (0.86 ml, 5.0 mmole), and 60% sodium hydride in mineral oil (0.11 g, 2.75 mmole) in dimethylformamide (100 mL) was stirred at 0° C. for 1 hour and heated at 45–50° C. under nitrogen for 24 hours. After cooling, the mixture was diluted with H2O and treated with 2N aqueous HCl until the mixture was clear. The clear solution was then extracted with dichloromethane. The organic layer was washed with H2O again, dried over anhydrous magnesium sulfate, and concentrated on a rotary evaporator. The residue was purified by chromatography on silica gel (30% dichloromethane/hexane) to give a clear oil as the expected product. The oily product was crystallized by triturated with hexane in a dry ice bath and collected at room temperature to give the title compound as a white solid, mp=88–90° C.; (−) ESI m/z=392 (M−H)−.

後処理

  1. temperatureheated at 45–50° C. under nitrogen for 24 hours
  2. temperatureAfter cooling
  3. extractionThe clear solution was then extracted with dichloromethane
  4. washThe organic layer was washed with H2O again
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated on a rotary evaporator
  7. customThe residue was purified by chromatography on silica gel (30% dichloromethane/hexane)

出典と根拠

ORDレコード
ord-ed791cb55edc45dcb6378ec25a4293e5
出典データセット
uspto-grants-2007_02
特許番号
US07179943B2

反応ノート

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