Ethylenediaminetetraacetic Acid → HCID 13116731, compound

HRID 2164733Notes

Reaction equation

[Cl-].[CH3:2][O:3][C:4](=[O:10])[CH2:5][CH2:6][C:7](O)=[O:8].[C:11]1([CH2:17][CH2:18][CH2:19][CH2:20][N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[Al+3].[Cl-].[Cl-].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.[OH-].[Na+]>ClCCCl>[CH3:2][O:3][C:4](=[O:10])[CH2:5][CH2:6][C:7]([C:14]1[CH:13]=[CH:12][C:11]([CH2:17][CH2:18][CH2:19][CH2:20][N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)=[CH:16][CH:15]=1)=[O:8]

Participants

Conditions

Temperature: 85 °C

Procedure

20.3 g of succinic acid methyl ester chloride and then a solution of 27 g of 1-(4-phenylbutyl)-imidazole in 100 ml of 1,2-dichloroethane are added dropwise to a suspension of 59.3 g of aluminium chloride in 200 ml of 1,2-dichloroethane, whilst cooling with ice. The mixture is then stirred at 85° C. for 3 hours. After it has been cooled, the reaction mixture is stirred into a mixture of 165.7 g of ethylenediaminetetraacetic acid and 600 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. The residue is purified by column chromatography (silica gel/chloroform).

Workup

temperaturewhilst cooling with ice
temperatureAfter it has been cooled
customThe phases are separated
dry with materialthe organic phase is dried over Na2SO4
concentrationconcentrated
customThe residue is purified by column chromatography (silica gel/chloroform)

Sources & evidence

ORD record: ord-a95b42b959264430939aaf61b4a679d7
Source dataset: uspto-grants-1985_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04507298

Reaction notes

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