Phosphorus trichloride → HCID 178527085, compound

HRID 867857Notes

Reaction equation

HRID 867857 reaction equation
[P:1]([OH:4])([OH:3])[OH:2].Cl.[NH:6]1[CH:10]=[C:9]([CH2:11][C:12]([OH:14])=O)[N:8]=[CH:7]1.P(Cl)(Cl)Cl>ClC1C=CC=CC=1>[OH:14][C:12]([P:1]([OH:4])(=[O:2])[OH:3])([P:1]([OH:4])(=[O:3])[OH:2])[CH2:11][C:9]1[N:8]=[CH:7][NH:6][CH:10]=1

Participants

5

Reactant 3

HCID 24387Phosphorus trichlorideHCID 107909Phosphorous acidHCID 178479752HCID 178479752, compound

Product 1

HCID 178527085HCID 178527085, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
110 °C

Procedure

3 g. Phosphorous acid are added to 3.5 g. imidazol4-ylacetic acid hydrochloride (m.p. 198-200° C.) in 40 ml. chlorobenzene. The reaction mixture is stirred for 10 minutes at 110° C., cooled and 9 g. phosphorus trichloride slowly added dropwise thereto. The reaction mixture is heated for 16 hours to 110° C., cooled, the chlorobenzene is decanted off from an orange-coloured syrup and the residue is mixed with 50 ml. 6N hydrochloric acid. The suspension is heated under reflux for 5 hours, cooled, mixed with charcoal and filtered off with suction. The filtrate is evaporated, dried and boiled up with acetone for 2 hours. The residue (4.3 g.) is dissolved in water, the solution is adjusted with 2N aqueous sodium hydroxide solution to a pH of 5, mixed with methanol and the precipitate obtained is filtered off with suction. There are obtained 1.2 g. (about 16.9% of theory) of the desired product; m.p.>290° C. The compound is obtained as the monosodium salt containing 2 moles of water of crystallisation (Mrel =0.37).

Workup

  1. temperaturecooled
  2. temperatureThe reaction mixture is heated for 16 hours to 110° C.
  3. temperaturecooled
  4. customthe chlorobenzene is decanted off from an orange-coloured syrup
  5. additionthe residue is mixed with 50 ml
  6. temperatureThe suspension is heated
  7. temperatureunder reflux for 5 hours
  8. temperaturecooled
  9. additionmixed with charcoal
  10. filtrationfiltered off with suction
  11. customThe filtrate is evaporated
  12. customdried
  13. waitboiled up with acetone for 2 hours
  14. dissolutionThe residue (4.3 g.) is dissolved in water
  15. additionmixed with methanol
  16. customthe precipitate obtained
  17. filtrationis filtered off with suction
  18. customThere are obtained 1.2 g

Sources & evidence

ORD record
ord-5420571409714e2e924da9b05090d0f6
Source dataset
uspto-grants-1988_10
Patent number
US04777163

Reaction notes

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