Hydrochloric Acid → HCID 20553585, compound

HRID 1106210Notes

Reaction equation

HRID 1106210 reaction equation
[Na][Na].[P:3]([CH2:7][NH:8][CH2:9][C:10]([OH:12])=[O:11])([OH:6])([OH:5])=[O:4].[CH2:13]([O:16][C:17](Cl)=[O:18])[CH:14]=[CH2:15].[OH-].[Na+].C1C=CC2C(C3C=CC(O)=CC=3)(C3C=CC(O)=CC=3)OC(=[O:29])C=2C=1.Cl>O>[OH2:4].[OH2:16].[OH2:29].[CH2:13]([O:16][C:17]([N:8]([CH2:7][P:3]([OH:6])([OH:5])=[O:4])[CH2:9][C:10]([OH:12])=[O:11])=[O:18])[CH:14]=[CH2:15]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4764PhenolphthaleinHCID 14798Sodium HydroxideHCID 18052Allyl chloroformateHCID 131712655HCID 131712655, compound

Product 1

HCID 20553585HCID 20553585, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution containing 10.7 g (0.05 mol) of disodium-N-phosphonomethylglycine in water at a temperature of 10°-15° C. was slowly added 6.6 g (0.055 mol) of allylchloroformate. While maintaining the temperature below 20° C., a 50% sodium hydroxide solution was slowly added to the reaction mixture until the pH of the resulting mixture stabilized at a phenolphthalein endpoint. While maintaining the temperature of the reaction mixture below 10° C., the reaction mixture was acidified using concentrated hydrochloric acid, filtered and the filtrate was then treated with ethanol. The treated filtrate was filtered to remove residual sodium chloride, then concentrated and the concentrate was passed over an acid Dowex-50 ion exchange resin. Methanol was added to the eluate forming a suspension. The suspension was filtered and the filtrate was chromatographed over acid Dowex-50 ion exchange resin. The eluate was concentrated and the residue was dried over potassium hydroxide in vacuo yielding a crude product. The crude product was broken up and redried at 100° C. and 1 mm Hg to yield N-allyloxycarbonyl-N-phosphonomethylglycine trihydrate (8.7 g; 57% yield) having the following analysis: Calculated: C, 27.37; H, 5.91; P, 10.08. Found: C, 27.05; H, 4.71; P, 9.76.

Workup

  1. temperatureWhile maintaining the temperature below 20° C.
  2. temperatureWhile maintaining the temperature of the reaction mixture below 10° C.
  3. filtrationfiltered
  4. additionthe filtrate was then treated with ethanol
  5. filtrationThe treated filtrate was filtered
  6. customto remove residual sodium chloride
  7. concentrationconcentrated
  8. additionMethanol was added to the eluate
  9. customforming a suspension
  10. filtrationThe suspension was filtered
  11. customthe filtrate was chromatographed over acid Dowex-50 ion exchange resin
  12. concentrationThe eluate was concentrated
  13. dry with materialthe residue was dried over potassium hydroxide in vacuo
  14. customyielding a crude product
  15. customredried at 100° C.

Sources & evidence

ORD record
ord-0cba1fa1367f4ab7aa883b8bf8dc0bd8
Source dataset
uspto-grants-1982_01
Patent number
US04312662

Reaction notes

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