Water → N-carboxymethyl-N-phosphonomethyl-2,3,4-tricarboxycyclobutanecarboxamide

HRID 1413646Notes

Reaction equation

HRID 1413646 reaction equation
[Na][Na].[P:3]([CH2:7][NH:8][CH2:9][C:10]([OH:12])=[O:11])([OH:6])([OH:5])=[O:4].[CH:13]12[C:25](=[O:26])[O:24][C:22](=[O:23])[CH:14]1[CH:15]1[C:20](=[O:21])[O:19][C:17](=[O:18])[CH:16]12.[OH2:27]>>[C:10]([CH2:9][N:8]([CH2:7][P:3]([OH:6])([OH:5])=[O:4])[C:17]([CH:16]1[CH:15]([C:20]([OH:19])=[O:21])[CH:14]([C:22]([OH:27])=[O:23])[CH:13]1[C:25]([OH:24])=[O:26])=[O:18])([OH:12])=[O:11]

Participants

5

Reactant 4

HCID 962WaterHCID 3496GlyphosateHCID 1072801,2,3,4-Cyclobutanetetracarboxylic dianhydrideHCID 141233Disodium

Product 1

HCID 20290082N-carboxymethyl-N-phosphonomethyl-2,3,4-tricarboxycyclobutanecarboxamide

Procedure

To a 28.6 grams (0.03 mole) portion of the disodium salt of N-phosphonomethylglycine, prepared as described in previous examples, there is added 4.2 grams (0.015 mole) of cyclobutane-1,2,3,4-tetracarboxylic dianhydride. A pH of about 8 is maintained with periodic additions of alkali, and further anhydride, in 4.2 grams and 1.0 gram portions, are added to complete the reaction. The reaction mixture is diluted with water and passed through a column of ion exchange resin in the acid form. The second through fourth 20 ml. cuts are collected and dried to yield N-carboxymethyl-N-phosphonomethyl-2,3,4-tricarboxycyclobutanecarboxamide (in the monohydrate form) as a cream colored brittle foam. Elemental analysis gives 33.38% carbon, 3.94% hydrogen, 3.27% nitrogen and 7.31% phosphorus as against calculated values of 32.93%, 4.02%, 3.49% and 7.72% for C11H14NO12P.H2O. ##STR21##

Workup

  1. additionin 4.2 grams and 1.0 gram portions, are added
  2. customthe reaction
  3. customcuts are collected
  4. customdried

Sources & evidence

ORD record
ord-1701792bc6b44c52858cf6b035da43cc
Source dataset
uspto-grants-1981_02
Patent number
US04251257

Reaction notes

Loading…