3-Methoxyaniline → N-(3-methoxyphenyl)-2-(3-pyridyl)thiazolidine-4-carboxamide

HRID 704427

反応式

HRID 704427 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[NH:11][CH:10]([C:12]([OH:14])=O)[CH2:9][S:8]2)[CH:2]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[CH:18]=1.C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([NH:23][C:12]([CH:10]2[CH2:9][S:8][CH:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[NH:11]2)=[O:14])[CH:20]=[CH:21][CH:22]=1

参加物

7

反応物 4

HCID 108243-MethoxyanilineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3275932-(3-Piridyl)thiazolidine-4-carboxylic acid

生成物 1

HCID 14881592N-(3-methoxyphenyl)-2-(3-pyridyl)thiazolidine-4-carboxamide収率 25.7%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 630 mg of 2-(3-pyridyl)thiazolidine-4-carboxylic acid, 350 mg of m-anisidine, 650 mg of dicyclohexylcarbodiimide and 430 mg of 1-hydroxybenzotriazole in 8 ml of dimethylformamide was stirred overnight at room temperature. The reaction mixture was diluted with 50 ml of ethyl acetate, and the insoluble matter was filtered off. The filtrate was washed with two portions of water, and then with aqueous solution of sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride in that order, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by preparative thin layer chromatography to give 230 mg of N-(3-methoxyphenyl)-2-(3-pyridyl)thiazolidine-4-carboxamide. This compound was dissolved in ethyl acetate, and 1 ml of 2N hydrogen chloride solution in dioxane was added. The resultant solid was collected by filtration, washed with ethyl acetate and dried to give 250 mg of N-(3-methoxyphenyl)-2-(3-pyridyl)thiazolidine-4-carboxamide dihydrochloride. Melting point 129° C.

後処理

  1. filtrationthe insoluble matter was filtered off
  2. washThe filtrate was washed with two portions of water
  3. dry with materialwith aqueous solution of sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride in that order, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by preparative thin layer chromatography

出典と根拠

ORDレコード
ord-54cb1d8a97614a4bb5fb4d7cea319536
出典データセット
uspto-grants-1991_01
特許番号
US04987132

関連ノート

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