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

반응식

[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]

참가 물질

반응물 4

HCID 8011Hydracrylonitrile

HCID 8028Tetrahydrofuran2회

HCID 8471Triethylamine

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

생성물 1

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

실험 절차

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.