Hydracrylonitrile → ethyl N-carbobenzoxy-N-[bis(beta-cyanoethoxy)phosphonomethyl]glycinate

Reaktionsgleichung

[C:1]([N:11]([CH2:18][P:19]([O:23]Cl)([O:21]Cl)=[O:20])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[C:25]([CH2:27][CH2:28][OH:29])#[N:26].C([N:32]([CH2:35][CH3:36])CC)C.[O:37]1CCC[CH2:38]1>>[C:1]([N:11]([CH2:18][P:19]([O:23][O:37][CH2:38][CH2:36][C:35]#[N:32])([O:21][O:29][CH2:28][CH2:27][C:25]#[N:26])=[O:20])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Komponenten

Edukt 4

HCID 8011Hydracrylonitrile

HCID 8028Tetrahydrofuran2×

HCID 8471Triethylamine

HCID 54297302ethyl N-carbobenzoxy-N-(dichlorophosphonomethyl)glycinate

Produkt 1

HCID 23332172ethyl N-carbobenzoxy-N-[bis(beta-cyanoethoxy)phosphonomethyl]glycinate

Versuchsvorschrift

Ethyl N-carbobenzoxy-N-(dichlorophosphonomethyl)glycinate (11.7 g., 0.032 mole) and 2-cyanoethanol (4.52 g., 0.064 mole) were dissolved in tetrahydrofuran (50 ml). To this solution was added triethylamine (6.42 g., 0.064 mole) dissolved in 25 ml. of tetrahydrofuran. The resultant solution was stirred overnight at room temperature. The reaction mixture was then filtered and the filtrate concentrated in vacuo to yield ethyl N-carbobenzoxy-N-[bis(β-cyanoethoxy)phosphonomethyl]glycinate as a yellow oil, ND25 =1.05 and having the following analysis.