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

HRID 2164394
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HRID 2164394 반응식
[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]
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참가 물질

7

반응물 5

HCID 6049Ethylenediaminetetraacetic AcidHCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 13120569HCID 13120569, 화합물HCID 86605420Succinic acid methylester chloride

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매2회

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1e702003e50c4be8b22fd604509cb481
출처 데이터셋
uspto-grants-1985_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04504479

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