Phosphorus trichloride → 1-Hydroxy-3-(4-imidazolyl)-propane-1,1-diphosphonic acid

HRID 1789159Notes

Reaction equation

HRID 1789159 reaction equation
Cl.[NH:2]1[CH:6]=[C:5]([CH2:7][CH2:8][C:9]([OH:11])=O)[N:4]=[CH:3]1.[P:12]([OH:15])([OH:14])[OH:13].P(Cl)(Cl)Cl>ClC1C=CC=CC=1>[OH:11][C:9]([P:12]([OH:15])(=[O:13])[OH:14])([P:12]([OH:15])(=[O:14])[OH:13])[CH2:8][CH2:7][C:5]1[N:4]=[CH:3][NH:2][CH:6]=1

Participants

5

Reactant 3

HCID 24387Phosphorus trichlorideHCID 107909Phosphorous acidHCID 178479756HCID 178479756, compound

Product 1

HCID 1785270861-Hydroxy-3-(4-imidazolyl)-propane-1,1-diphosphonic acid

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

3.53 g. (20 mMol) 3-(4-imidazolyl)-propionic acid hydrochloride are heated with 2.26 g. phosphorous acid in 10 ml. chlorobenzene to 110° C., while stirring. 4.12 g. (30 mMol) phosphorus trichloride are slowly added dropwise thereto and heating continued for 4 hours at 110° C. After cooling, the chlorobenzene is decanted off and the residue boiled under reflux for 5 hours with 15 ml. 6N hydrochloric aci. The reaction mixture is allowed to cool, mixed with active charcoal, filtered and the filtrate evaporated. The residue is taken up in 10 ml. water, the solution is adjusted with an aqueous solution of sodium bicarbonate to a pH value of 5.5 and mixed with methanol until no further precipitate is formed. The precipitate is filtered off with suction, washed with methanol and dried. There are obtained 3.23 g. (48% of theory) of the title compound. The product is obtained as the monosodium salt with 1 mole of water of crystallisation.

Workup

  1. temperatureheating
  2. temperatureAfter cooling
  3. customthe chlorobenzene is decanted off
  4. temperatureunder reflux for 5 hours with 15 ml
  5. temperatureto cool
  6. additionmixed with active charcoal
  7. filtrationfiltered
  8. customthe filtrate evaporated
  9. additionmixed with methanol until no further precipitate
  10. customis formed
  11. filtrationThe precipitate is filtered off with suction
  12. washwashed with methanol
  13. customdried
  14. customThere are obtained 3.23 g

Sources & evidence

ORD record
ord-9e3f18cd9f6049a2b27c425d1d3375db
Source dataset
uspto-grants-1987_08
Patent number
US04687767

Reaction notes

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