Ethylenediaminetetraacetic Acid → 4-[5-(1-Imidazolylmethyl)-thien-2-yl]-4-oxo-butyric acid methyl ester
Reaction equation
[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]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
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.
Workup
- temperaturewhilst cooling with ice
- temperatureAfter it has been cooled
- customThe phases are separated
- dry with materialthe organic phase is dried over Na2SO4
- concentrationconcentrated
- extractionExtraction of the residue
- stirringby stirring with hexane
- customgives colourless crystals
Sources & evidence
- ORD record
- ord-1e702003e50c4be8b22fd604509cb481
- Source dataset
- uspto-grants-1985_03
- Patent number
- US04504479
Reaction notes
Loading…