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Diphenylphosphinic chloride → 3-[2-(4-Geranyloxybenzoylamino)ethylamino]pyridine

HRID 850404
ノート
印刷プレビュー

反応式

HRID 850404 の反応式
[CH2:1]([O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.[NH2:36][CH2:37][CH2:38][NH:39][C:40]1[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:1]([O:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([NH:36][CH2:37][CH2:38][NH:39][C:40]2[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=2)=[O:18])=[CH:19][CH:20]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])\[CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 73910Diphenylphosphinic chlorideHCID 123615004-Geranyloxybenzoic acidHCID 14834213N-pyridin-3-ylethane-1,2-diamine

生成物 1

HCID 154342383-[2-(4-Geranyloxybenzoylamino)ethylamino]pyridine収率 47.1%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒
HCID 8471
Triethylamine
溶媒

実験手順

4-geranyloxybenzoic acid(3.57 g) was dissolved in chloroform(60 ml) and triethylamine(3.60 ml), and then diphenylphosphinic chloride(2.48 ml) was added thereto while being cooled with ice. After being stirred for 30 minutes, the mixture, with 3-(2-aminoethylamino)pyridine(2.24 g) added thereto, was stirred for 3 hours at room temperature. The reaction mixture was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was purified by silica gel column chromatography (chloroform:methanol=15:1). The resulting solid was recrystallized from n-hexane/ethyl acetate, thereby yielding 2.41 g of the aimed compound.

後処理

  1. temperaturewhile being cooled with ice
  2. stirringwas stirred for 3 hours at room temperature
  3. washThe reaction mixture was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  4. dry with materialdried over sodium sulfate anhydride
  5. concentrationconcentrated under a vacuum
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=15:1)
  7. customThe resulting solid was recrystallized from n-hexane/ethyl acetate

出典と根拠

ORDレコード
ord-f90557e5dfe54d1e893bda4a73f7bf62
出典データセット
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06017937

反応ノート

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