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

HRID 1883259Notes

Reaction equation

[C:1]([N:4]([CH2:6][C:7]([OH:9])=[O:8])[CH3:5])(=O)C.[P:10]([OH:13])([OH:12])[OH:11].Cl.C=O>>[P:10]([CH2:1][N:4]([CH3:5])[CH2:6][C:7]([OH:9])=[O:8])([OH:13])([OH:12])=[O:11]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 712Formaldehyde

HCID 107909Phosphorous acid

HCID 10975514N-Acetyl-N-methylglycine

Product 1

HCID 541499N-methyl-N-(phosphonomethyl)glycineYield 99%

Conditions

Temperature: 120 °C

Procedure

N-acetyl sarcosine (XX) (20.0 g, 152.5 mmole), phosphorous acid (12.59, 152.4 mmole), and concentrated HCl (37.6 g) were mixed and refluxed in a 120° C. oil bath. Formalin, 37% (13.6 g, 167.6 mmole) was added dropwise over 20 min. and the reaction was continued for an additional 19 h. HPLC analysis indicated a-99% yield of N-methylglyphosate (XXI) based on moles of (XX) charged.

Sources & evidence

ORD record: ord-3d95f3a6fd50403fb5bdf571eec7565c
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06759549B2

Reaction notes

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