Acrylonitrile → 9-(2-Cyanoethyl)-9H-fluorene-9-carboxamide

HRID 893917

반응식

HRID 893917 반응식
[C:1]([CH:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:3])[NH2:2].O1CCOCC1.[OH-].[CH2:24]([N+:31](C)(C)C)[C:25]1C=CC=C[CH:26]=1.C(#N)C=C>CO>[C:1]([C:4]1([CH2:26][CH2:25][C:24]#[N:31])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:3])[NH2:2]

참가 물질

6

반응물 4

HCID 7855AcrylonitrileHCID 312751,4-DioxaneHCID 66854Benzyltrimethylammonium hydroxideHCID 3450289H-fluorene-9-carboxamide

생성물 1

HCID 30188199-(2-Cyanoethyl)-9H-fluorene-9-carboxamide

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
70 °C

실험 절차

A 4.2 g. portion of 9-carbamoylfluorene was dissolved in 300 ml. of dioxane at 45° C. To the solution was added 0.4 ml. of Triton B (40% benzyltrimethylammonium hydroxide in methanol) and 1.1 g. of acrylonitrile. The reaction mixture was stirred at 70° C. for one hour and was then allowed to cool to ambient temperature and stand overnight. The dioxane was removed under vacuum, and the remaining oil was taken up in ethyl acetate/water. The layers were separated, and the organic layer was washed three times with water and once with saturated sodium chloride solution. The organic layer was then dried over magnesium sulfate, filtered and evaporated under vacuum to a foam, which was taken up in dichloromethane. The solution was boiled, and hexane was added until crystallization occurred. The mixture was chilled overnight, and the crystals were collected by filtration. The crystals were washed with hexane and dried under vacuum at 40° to obtain 3.2 g. of the desired product, m.p. 148°-152°, with sintering at 143°.

후처리

  1. customat 45° C
  2. additionTo the solution was added 0.4 ml
  3. temperatureto cool to ambient temperature
  4. waitstand overnight
  5. customThe dioxane was removed under vacuum
  6. customThe layers were separated
  7. washthe organic layer was washed three times with water
  8. dry with materialThe organic layer was then dried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated under vacuum to a foam, which
  11. additionhexane was added until crystallization
  12. temperatureThe mixture was chilled overnight
  13. filtrationthe crystals were collected by filtration
  14. washThe crystals were washed with hexane
  15. customdried under vacuum at 40°
  16. customto obtain 3.2 g

출처 및 근거

ORD 기록
ord-ce49afb6eb7a4157b8310af93e6075b3
출처 데이터셋
uspto-grants-1981_08
특허 번호
US04282170

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