Sodium hydride → HCID 20251327, compound
Reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:28])[C:7]([CH2:19][CH2:20][O:21][CH2:22][CH2:23]OCCI)(CCOCCOCCI)[C:8]#[N:9])[CH3:4]>O1CCCC1>[C:8]([CH:7]([C:6]([O:5][CH2:3][CH3:4])=[O:28])[CH2:19][CH2:20][O:21][CH:22]([O:21][CH2:20][CH2:19][CH:7]([C:6]([O:5][CH2:3][CH3:4])=[O:28])[C:8]#[N:9])[CH3:23])#[N:9]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
0.19 g (4 mmol) of sodium hydride was added to 20 ml of dry tetrahydrofuran, and to this solution was added dropwise, while refluxing under heating, a solution formed by dissolving 0.6 g (1 mmol) of bis(8-iodo-3,6-dioxaoctyl)cyanoacetic acid ethyl ester obtained in the above-said preparation process and 0.34 g (1 mmol) of bis(3-cyano-3-carboethoxypropoxy)ethane in 20 ml of tetrahydrofuran, by using a specific dropping apparatus for the high dilution reactions (an apparatus designed to dilute the dropping solution with the refluxing solvent) over the period of 24 hours. After completion of said dropwise addition, reflux was continued for further 12 hours. After neutralizing the solution with dilute hydrochloric acid, tetrahydrofuran was distilled off and the residue was extracted with ether. Then ether was distilled off and the resultant oily residue was separated by basic alumina-packed column chromatography by using benzene-tetrahydrofuran (2:1) as eluent, obtaining 0.17 g of tricyanotricarboxylic acid triethyl ester (yield: 25%). The property analyses of this compound gave the following results.
Workup
- additionto this solution was added dropwise
- temperaturewhile refluxing
- temperatureunder heating
- customa solution formed
Sources & evidence
- ORD record
- ord-5ae5ea77c0bc48b5b704ba815d820331
- Source dataset
- uspto-grants-1986_01
- Patent number
- US04564690
Reaction notes
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