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

HRID 1649791ノート

反応式

HRID 1649791 の反応式
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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒HCID 21863594Toluene ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f82c52a647f04a55a9d54a0117cf832c
出典データセット
uspto-grants-1990_05
特許番号
US04921867

反応ノート

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