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

HRID 224224

Reaction equation

HRID 224224 reaction equation
[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]

Participants

5

Reactant 4

HCID 8011HydracrylonitrileHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 54297302ethyl N-carbobenzoxy-N-(dichlorophosphonomethyl)glycinate

Product 1

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

Procedure

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.

Workup

  1. dissolutiondissolved in 25 ml
  2. filtrationThe reaction mixture was then filtered
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-e13ee0364e1244808fb144af690deaa4
Source dataset
uspto-grants-1980_11
Patent number
US04231782

Linked notes

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