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Ethylenediaminetetraacetic Acid → 4-[5-(1-Imidazolylmethyl)-thien-2-yl]-4-oxo-butyric acid methyl ester

HRID 2164394
ノート
印刷プレビュー

反応式

HRID 2164394 の反応式
[Cl-].[CH3:2][O:3][C:4](=[O:10])[CH2:5][CH2:6][C:7](O)=[O:8].[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH2:16]N1C=CN=C1.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:26]([N:37]([CH2:42]C(O)=O)CC(O)=O)[CH2:27][N:28](CC(O)=O)CC(O)=O.[OH-].[Na+]>ClCCCl>[CH3:2][O:3][C:4](=[O:10])[CH2:5][CH2:6][C:7]([C:15]1[S:11][C:12]([CH2:16][C:42]2[NH:37][CH:26]=[CH:27][N:28]=2)=[CH:13][CH:14]=1)=[O:8]
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

7

反応物 5

HCID 6049Ethylenediaminetetraacetic AcidHCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 13120569HCID 13120569、化合物HCID 86605420Succinic acid methylester chloride

生成物 1

HCID 704876864-[5-(1-Imidazolylmethyl)-thien-2-yl]-4-oxo-butyric acid methyl ester

試薬・触媒・溶媒

1
HCID 111,2-Dichloroethane溶媒2 回

反応条件

温度
50 °C

実験手順

19.5 g of succinic acid methyl ester chloride and then a solution of 20 g of 1-(thien-2-ylmethyl)-imidazole in 200 ml of 1,2-dichloroethane are added dropwise to a suspension of 53.5 g of aluminium chloride in 240 ml of 1,2-dichloroethane, whilst cooling with ice. The mixture is then stirred at 50° C. for 3 hours. After it has been cooled, the reaction mixture is stirred into a mixture of 147.3 g of ethylenediaminetetraacetic acid and 500 g of ice and is brought to about pH 8 by addition of dilute sodium hydroxide solution. The phases are separated and the organic phase is dried over Na2SO4 and concentrated. Extraction of the residue by stirring with hexane gives colourless crystals.

後処理

  1. temperaturewhilst cooling with ice
  2. temperatureAfter it has been cooled
  3. customThe phases are separated
  4. dry with materialthe organic phase is dried over Na2SO4
  5. concentrationconcentrated
  6. extractionExtraction of the residue
  7. stirringby stirring with hexane
  8. customgives colourless crystals

出典と根拠

ORDレコード
ord-1e702003e50c4be8b22fd604509cb481
出典データセット
uspto-grants-1985_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04504479

反応ノート

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