Methane → 2-[6-[(6-Bromohexyl)oxy]-1-hexynyl]-4-pyridinecarboxamide

HRID 1649791노트

반응식

HRID 1649791 반응식
Br[C:2]1[CH:7]=[C:6]([C:8]([NH2:10])=[O:9])[CH:5]=[CH:4][N:3]=1.[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[CH:24].C1(NC2CCCCC2)CCCCC1.C>C(#N)C.CCOCC.C(O)C.C1(C)C=CC=CC=1.[Cu]I>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[C:24][C:2]1[CH:7]=[C:6]([C:8]([NH2:10])=[O:9])[CH:5]=[CH:4][N:3]=1

참가 물질

9

반응물 4

HCID 297MethaneHCID 7582DicyclohexylamineHCID 46254072-BromoisonicotinamideHCID 218671586-[(6-Bromohexyl)oxy]-1-hexyne

생성물 1

HCID 198547972-[6-[(6-Bromohexyl)oxy]-1-hexynyl]-4-pyridinecarboxamide

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매HCID 21863594Toluene ethanol용매

실험 절차

A mixture of 2-bromo-4-pyridinecarboxamide (1.1 g), BTPC (35 mg), copper (I) iodide (8 mg), 6-[(6-bromohexyl)oxy]-1-hexyne (1.43 g) and dicyclohexylamine (1.2 ml) in acetonitrile (20 ml) was stirred at room temperature, under nitrogen, for 20 h, then left to stand for 24 h. The yellow mixture was diluted with ether (50 ml), filtered, the filtrate dried and evaporated in vacuo to give a yellow waxy solid. The solid was purified by FCC eluting with System A (98:2:1) to give a pale yellow waxy solid. The solid was dissolved in ethanol:toluene (1:1), (20 ml) treated with activated charcoal (0.2 g), heated, filtered through hyflo and evaporated in vacuo to give the title compound as a pale yellow waxy solid (1.04 g), t.l.c. (toluene-ethanol: 0.880 ammonia, 90:10:1) Rf 0.31.

후처리

  1. waitleft
  2. waitto stand for 24 h
  3. filtrationfiltered
  4. customthe filtrate dried
  5. customevaporated in vacuo
  6. customto give a yellow waxy solid
  7. customThe solid was purified by FCC
  8. washeluting with System A (98:2:1)
  9. customto give a pale yellow waxy solid
  10. temperatureheated
  11. filtrationfiltered through hyflo
  12. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-f82c52a647f04a55a9d54a0117cf832c
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04921867

반응 노트

불러오는 중…