Formaldehyde → N-methyl-N-(phosphonomethyl)glycine

HRID 1883260Notes

Reaction equation

HRID 1883260 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].S(=O)(=O)(O)O.C=O>O>[P:10]([CH2:1][N:4]([CH3:5])[CH2:6][C:7]([OH:9])=[O:8])([OH:13])([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 107909Phosphorous acidHCID 10975514N-Acetyl-N-methylglycine

Product 1

HCID 541499N-methyl-N-(phosphonomethyl)glycineYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

N-acetyl sarcosine (XX)(2.0 g, 15.3 mmole), phosphorous acid (1.25 g, 15.3 mmole) were mixed with concentrated sulfuric acid (3.1 g) and water (1.7 g) then refluxed in a 120° C. oil bath. Formalin, 37% (1.4 g, 16.7 mmole) was added dropwise over 20 min. and the reaction was continued for an additional 18 h. 31P NMR analysis indicated 98% yield of (XXI) based on mmoles of (XX) charged.

Sources & evidence

ORD record
ord-8504f2d4a52142e7833f311ff5f4af1f
Source dataset
uspto-grants-2004_07
Patent number
US06759549B2

Reaction notes

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