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4-Amino-5-chloro-2-methoxybenzoic acid → 4-amino-5-chloro-N-[(4-ethoxycarbonyl-2-morpholinyl)methyl]-2-methoxybenzamide

HRID 1608190
ノート
印刷プレビュー

反応式

HRID 1608190 の反応式
[NH2:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4]1.[NH2:14][C:15]1[C:23]([Cl:24])=[CH:22][C:18]([C:19](O)=[O:20])=[C:17]([O:25][CH3:26])[CH:16]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[NH2:14][C:15]1[C:23]([Cl:24])=[CH:22][C:18]([C:19]([NH:1][CH2:2][CH:3]2[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4]2)=[O:20])=[C:17]([O:25][CH3:26])[CH:16]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14877395Ethyl 2-(aminomethyl)morpholine-4-carboxylate

生成物 1

HCID 148773964-amino-5-chloro-N-[(4-ethoxycarbonyl-2-morpholinyl)methyl]-2-methoxybenzamide収率 81.3%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

反応条件

温度
25 °C

実験手順

To a solution of 2-aminomethyl-4-ethoxycarbonylmorpholine (5.8 g) in dichloromethane (100 ml), 4-amino-5-chloro-2-methoxybenzoic acid (5.0 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.2 g) are added, and the resulting mixture is stirred at 25° C. for 4 hours. The reaction mixture is washed successively with water, aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent is distilled off under reduced pressure. The residue is dissolved in chloroform and chromatographed on silica gel. The eluate with chloroform is discarded, and the subsequent eluates with methanol-chloroform (1:9) are pooled and evaporated to give the title compound (7.5 g) as an oil.

後処理

  1. washThe reaction mixture is washed successively with water, aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. distillationThe solvent is distilled off under reduced pressure
  4. dissolutionThe residue is dissolved in chloroform
  5. customchromatographed on silica gel
  6. customevaporated

出典と根拠

ORDレコード
ord-50147ce3283a4e3f91f06ffb648bcc5a
出典データセット
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04870074

反応ノート

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