Hydrochloric Acid → Glycine, N-[(dimethoxyphosphinyl)methyl]-

HRID 462123Notes

Reaction equation

HRID 462123 reaction equation
[CH2:1]=O.[OH-].[Na+].[NH2:5][CH2:6][C:7]([OH:9])=[O:8].[P:10]([O-:15])([O:13][CH3:14])[O:11][CH3:12].Cl>O>[C:7]([CH2:6][NH:5][CH2:1][P:10](=[O:15])([O:13][CH3:14])[O:11][CH3:12])([OH:9])=[O:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 750GlycineHCID 14798Sodium HydroxideHCID 21884954Dimethylphosphite

Product 1

HCID 10856418Glycine, N-[(dimethoxyphosphinyl)methyl]-

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 at 0° to 5° C. After 10 minutes of stirring 11 g. (0.1 moles) of dimethyl 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 dimethyl N-carboxymethyl-aminomethyl-phosphonate. The hygroscopic product melts at 73°-75° with decomposition.

Workup

  1. customat 0° to 5° C
  2. stirringstirring
  3. waitis continued for 2 hours at 90° to 100° C
  4. temperatureThe reaction mixture is cooled
  5. extractionextracted

Sources & evidence

ORD record
ord-03985ae384bc42419da5ab399023c486
Source dataset
uspto-grants-1977_12
Patent number
US04065491

Reaction notes

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