HCID 10497707, compound → Glyphosate

HRID 972552Notes

Reaction equation

HRID 972552 reaction equation
C(CN1CN(CC(OCC)=O)CN(CC(OCC)=O)C1)(OCC)=O.COC1C=CC(OP([O-])OC2C=CC(OC)=CC=2)=CC=1.COC1C=CC(O[C:52](OC2C=CC(OC)=CC=2)([P:60]([OH:63])([OH:62])=[O:61])[NH:53][CH2:54][C:55]([O:57]CC)=[O:56])=CC=1>Cl>[P:60]([CH2:52][NH:53][CH2:54][C:55]([OH:57])=[O:56])([OH:63])([OH:62])=[O:61]

Participants

5

Reactant 3

HCID 10497707HCID 10497707, compoundHCID 20358965HCID 20358965, compoundHCID 22764498HCID 22764498, compound

Product 1

HCID 3496Glyphosate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
80 °C

Procedure

1,3,5-Tricarbethoxymethylhexahydro-1,3,5-triazine (5.76 parts) and di(4-methoxyphenyl)phosphite (15.3 parts containing 0.6 parts of 4-methoxyphenol) were mixed and heated to 80° C. for from 1/2 to 1 hour. Nuclear magnetic resonance spectral analysis indicated that a complete conversion to the ethyl N-[di(4-methoxyphenoxy)-phosphonomethyl]glycinate was obtained. The reaction mixture can then be diluted with 2 normal hydrochloric acid (225 ml) and heated to reflux for 2 hours. This reaction mixture is concentrated and then mixed with a mixture of water and methylene chloride. The water layer is then extracted with methylene chloride. The aqueous layer is concentrated to yield N-phosphonomethyl glycine.

Workup

  1. customwas obtained
  2. temperatureheated
  3. temperatureto reflux for 2 hours
  4. concentrationThis reaction mixture is concentrated
  5. additionmixed with a mixture of water and methylene chloride
  6. extractionThe water layer is then extracted with methylene chloride
  7. concentrationThe aqueous layer is concentrated

Sources & evidence

ORD record
ord-c420a2d7ab1c44fe8efd3bcd984ca196
Source dataset
uspto-grants-1977_10
Patent number
US04053505

Reaction notes

Loading…