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

HRID 349789노트

반응식

HRID 349789 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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)−.

후처리

  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)

출처 및 근거

ORD 기록
ord-ed791cb55edc45dcb6378ec25a4293e5
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179943B2

반응 노트

불러오는 중…