Methanol → Incadronic acid

HRID 2107344Notes

Reaction equation

HRID 2107344 reaction equation
C([O:3][P:4]([CH:9]([NH:18][CH:19]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]=[CH:20]1)[P:10](=[O:17])([O:14]CC)[O:11]CC)(=[O:8])[O:5]CC)C.CO.O>C(Cl)(Cl)(Cl)Cl>[CH2:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:19]1[NH:18][CH:9]([P:10](=[O:11])([OH:14])[OH:17])[P:4](=[O:3])([OH:5])[OH:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 14884334HCID 14884334, compound

Product 1

HCID 3699Incadronic acidYield 34.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2.5 ml of trimethylsililiodide was added dropwise to an ice-cold solution of 1.55 g of tetraethyl(2-cycloheptenyl)aminomethylenebis(phosphonate) in 25 ml of carbon tetrachloride. Then, the mixture was stirred at room temperature for 2.5 hours. 2 ml of methanol and 1 ml of purified water were added to the ice-cold reaction solution and it was concentrated under reduced pressure. To the obtained residue were added methanol and acetone to give a white solid. The residue was recrystallized from water-methanol to give 0.39 g of (2-cycloheptyl)aminomethylenebis(phosphonic acid) as colorless crystals in the form of needles.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionTo the obtained residue were added methanol and acetone
  3. customto give a white solid
  4. customThe residue was recrystallized from water-methanol

Sources & evidence

ORD record
ord-b06611bbc102417e86a5cedcfcbaa65e
Source dataset
uspto-grants-1990_06
Patent number
US04933472

Reaction notes

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