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1,1'-Carbonyldiimidazole → N-(2,6-dihydroxyphenyl)-3-cyclopentyloxy-4-methoxyphenylacetamide

HRID 1377547
ノート
印刷プレビュー

反応式

HRID 1377547 の反応式
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][C:16]([OH:18])=O)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:31][C:32]1[C:38]([OH:39])=[CH:37][CH:36]=[CH:35][C:33]=1[OH:34]>ClCCl.O>[OH:34][C:33]1[CH:35]=[CH:36][CH:37]=[C:38]([OH:39])[C:32]=1[NH:31][C:16](=[O:18])[CH2:15][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:8]=1
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 682631,1'-CarbonyldiimidazoleHCID 694512-AminoresorcinolHCID 107293423-Cyclopentyloxy-4-methoxyphenylacetic acid

生成物 1

HCID 22618291N-(2,6-dihydroxyphenyl)-3-cyclopentyloxy-4-methoxyphenylacetamide収率 60%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6344
Dichloromethane
溶媒
2 回

実験手順

A suspension of 3-cyclopentyloxy-4-methoxyphenylacetic acid (2.49 g) and 1,1'-carbonyldiimidazole (2.31 g) in dichloromethane (10 ml) was stirred at room temperature, under argon, for 2 hours. The resulting solution was added to a stirred suspension of 2-aminoresorcinol (1.62 g) in dichloromethane (15 ml) and the mixture stirred at room temperature, under argon, overnight. The reaction mixture was diluted with water (100 ml) and extracted with dichloromethane (3×50 ml). The combined organic extracts were washed with water (100 ml), 1N HCl (100 ml) and brine (100 ml), dried over CaSO4 and evaporated in-vacuo to yield the title compound (2.122 g, 60%) as a beige solid. δH (250MHz;d6DMSO) 1.53-1.95 (SH,m,4×CH2), 3.65 (2H, s,CH2), 3.70 (3H,s,OMe), 4.75 (1H,m, CH), 6.3 (1H,s,ArH), 6.35 (1H,s,ArH), 6.90 (4H,m,ArH), 9.40 (2H,s,ArOH), 9.6 (1H,s,CONH).

後処理

  1. stirringthe mixture stirred at room temperature, under argon, overnight
  2. extractionextracted with dichloromethane (3×50 ml)
  3. washThe combined organic extracts were washed with water (100 ml), 1N HCl (100 ml) and brine (100 ml)
  4. dry with materialdried over CaSO4
  5. customevaporated in-vacuo

出典と根拠

ORDレコード
ord-5ec2ccbd8c5a4d6f9eadd35a35f9f4d6
出典データセット
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05665737

反応ノート

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