Hydrochloric Acid → N-methyl-N-(phosphonomethyl)glycine

HRID 1883239Notes

Reaction equation

HRID 1883239 reaction equation
Cl.[C:2]([N:5]([CH2:7][C:8]([OH:10])=[O:9])[CH3:6])(=O)C.N(CC(O)=O)C.C=O.[OH:19][PH:20]([OH:22])=[O:21].P(Cl)(Cl)Cl>C(O)(=O)C.O>[P:20]([CH2:2][N:5]([CH3:6])[CH2:7][C:8]([OH:10])=[O:9])([OH:22])([OH:21])=[O:19]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 407Phosphonic acid2×HCID 712FormaldehydeHCID 1088Sarcosine2×HCID 24387Phosphorus trichlorideHCID 10975514N-Acetyl-N-methylglycine

Product 1

HCID 541499N-methyl-N-(phosphonomethyl)glycine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

As depicted, one equivalent of N-methylacetamide IX is reacted with one equivalent each of carbon monoxide and formaldehyde in the presence of a carboxymethylation catalyst precursor and solvent to yield N-acetylsarcosine XX. In the presence of water and an acid such as hydrochloric acid, N-acetylsarcosine XX is hydrolyzed to sarcosine XXIII and acetic acid. Sarcosine XXIII is reacted with formaldehyde and H3PO3, PCl3 or other H3PO3 source to produce N-(phosphonomethyl)-N-methyl-glycine XXI which is oxidized in the presence of a platinum catalyst and oxygen to glyphosate I.

Sources & evidence

ORD record
ord-5d99f3f950ee48a08217d9115d54d7b6
Source dataset
uspto-grants-2004_07
Patent number
US06759549B2

Reaction notes

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