3,4,5,6-Tetrahydrophthalic anhydride → Glyphosate

HRID 1413644Notes

Reaction equation

HRID 1413644 reaction equation
C1(=O)OC(=O)C2CCCCC1=2.[OH-].[Na+:13].C([O-])(=O)C1C=CCCC1C([O-])=O.[Na+:26].[Na+].C1C(N=NC2C(=O)N(C3C=CC(S([O-])(=O)=O)=CC=3)N=C2C([O-])=O)=CC=C(S([O-])(=O)=O)C=1.[Na+].[Na+].[Na+].[C:62]([CH2:65][N:66]([CH2:78][P:79]([OH:82])([OH:81])=[O:80])C(=O)C1CCCCC=1C(O)=O)([OH:64])=[O:63]>>[Na:13][Na:26].[P:79]([CH2:78][NH:66][CH2:65][C:62]([OH:64])=[O:63])([OH:82])([OH:81])=[O:80]

Participants

7

Reactant 5

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 14798Sodium HydroxideHCID 164825TartrazineHCID 20290069Disodium tetrahydrophthalateHCID 20290081N-carboxymethyl-N-phosphonomethyl-3,4,5,6-tetrahydrophthalamic acid

Product 2

HCID 3496GlyphosateHCID 141233Disodium

Procedure

The disodium salt of N-phosphonomethylglycine is prepared as described in Example III. The salt solution is stirred while 8.5 grams of 3,4,5,6-tetrahydrophthalic anhydride is added, along with sodium hydroxide to maintain the pH above 8. The reaction mixture is rotated overnight, after which a further 1.0 gram of anhydride is added and the reaction mixture stirred to completion. The mixture is filtered to yield a pink solution containing some disodium tetrahydrophthalate as a by-product. The reaction product is identified by nmr as the trisodium salt of N-carboxymethyl-N-phosphonomethyl-3,4,5,6-tetrahydrophthalamic acid. ##STR6##

Workup

  1. temperatureto maintain the pH above 8
  2. filtrationThe mixture is filtered
  3. customto yield a pink solution

Sources & evidence

ORD record
ord-b64d81511d1742b6b025c13c3ff9111b
Source dataset
uspto-grants-1981_02
Patent number
US04251257

Reaction notes

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