Sodium Hydroxide → HCID 20290078, compound

HRID 2049233Notes

Reaction equation

HRID 2049233 reaction equation
[P:1]([CH2:5][NH:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])([OH:4])([OH:3])=[O:2].[OH-].[Na+].[CH3:15][CH:16]1[CH2:21][C:20](=[O:22])[O:19][C:17]1=[O:18]>O>[C:8]([CH2:7][N:6]([CH2:5][P:1]([OH:4])([OH:3])=[O:2])[C:20](=[O:22])[CH2:21][CH:16]([CH3:15])[C:17]([OH:19])=[O:18])([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 20051Methylsuccinic anhydrideHCID 10965464HCID 10965464, compound

Product 1

HCID 20290078HCID 20290078, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A suitable reaction vessel is charged with 3.94 grams (0.02 mole) of ethyl N-phosphonomethylglycinate in 15 ml. of water. While cooling below about 15° C. in an icebath, 50% aqueous sodium hydroxide is added to obtain a pH of about 8. There is then added 2.51 grams (0.022 mole) of methylsuccinic anhydride with stirring and continued cooling. Two further 1.0 gram portions of anhydride are added to complete the reaction, the pH being maintained with additional alkali. The reaction mixture is diluted with water and passed through a column of ion exchange resin in the acid form. The first seven 20 ml. cuts are combined in 20 ml. of water, and a further 1.2 gram portion of anhydride is added. The resultant reaction mixture is passed through the column, and the first four 20 ml. cuts are combined and dried. The product is cooled in dry ice to yield N-carbethoxymethyl-N-(phosphonomethyl)-2-methylsuccinamic acid (in the monohydrate form) as a clear glass-gum. Elemental analysis gives 4.01% nitrogen and 9.13% phosphorus as against calculated values of 4.25% and 9.40% for C10H18NO8P.H2O. ##STR18##

Workup

  1. additionis added
  2. customto obtain a pH of about 8
  3. temperaturecontinued cooling
  4. customthe reaction
  5. temperaturethe pH being maintained with additional alkali
  6. customThe resultant reaction mixture
  7. customdried
  8. temperatureThe product is cooled in dry ice

Sources & evidence

ORD record
ord-b7a1bb4e06aa4499b61a360f4c3c268e
Source dataset
uspto-grants-1980_04
Patent number
US04197254

Reaction notes

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