Hydrochloric Acid → N-[(Diethoxyphosphoryl)methyl]glycine

HRID 462124Notes

Reaction equation

HRID 462124 reaction equation
[CH2:1]=O.[OH-].[Na+].[NH2:5][CH2:6][C:7]([OH:9])=[O:8].[P:10]([O-:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13].Cl>O>[C:7]([CH2:6][NH:5][CH2:1][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])([OH:9])=[O:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 750GlycineHCID 14798Sodium HydroxideHCID 3780918Diethylphosphite

Product 1

HCID 12633685N-[(Diethoxyphosphoryl)methyl]glycine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.6 g. of 37% formaline (= 0.1 moles of formaldehyde) are added to a stirred solution of 4.0 g. (0.1 moles) of sodium hydroxide and 7.5 g. (0.1 moles) of glycine in 40 ml. of water. After 10 minutes of stirring at 0° to 5° C, 13.8 g. (0.1 moles) of diethyl phosphite are added, and stirring is continued for 2 hours at 90° to 100° C. The reaction mixture is cooled, acidified with hydrochloric acid, and extracted to obtain diethyl N-carboxymethyl-aminomethyl-phosphonate. The product melts at 132°-134° C with decomposition.

Workup

  1. stirringstirring
  2. waitis continued for 2 hours at 90° to 100° C
  3. temperatureThe reaction mixture is cooled
  4. extractionextracted

Sources & evidence

ORD record
ord-83514d4ba6024be197015d87d5858cdf
Source dataset
uspto-grants-1977_12
Patent number
US04065491

Reaction notes

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