HCID 9934281, compound → HCID 15227683, compound

HRID 1492888Notes

Reaction equation

HRID 1492888 reaction equation
[C:1]1([S:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH:13]([P:22](=[O:29])([O:26]CC)[O:23]CC)[P:14](=[O:21])([O:18]CC)[O:15]CC)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>Cl>[C:1]1([S:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH:13]([P:22](=[O:23])([OH:26])[OH:29])[P:14](=[O:15])([OH:18])[OH:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 9934281HCID 9934281, compound

Product 1

HCID 15227683HCID 15227683, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Tetraethyl 4-(phenylthio)butylaminomethylenebisphosphonate (11.1 g) was dissolved in concentrated hydrochloric acid (150 ml) and the mixture was refluxed for 2.5 hours. After the reaction mixture was concentrated under reduced pressure, water was poured and separated crystals were collected by filtration to obtain 4-(phenylthio)butylaminomethylenebisphosphonic acid (4.94 g) as a white powder. Sodium methylate (28% methanol solution, 13.3 g) was added to the suspension of this powder (4.08 g) in methanol (50 ml), and the resultant was stirred at room temperature for one hour and then concentrated under reduced pressure. Methanol was added to the residue, the separated white crystals were collected by filtration and recrystallized from water-methanol to obtain tetrasodium 4-(phenylthio)butylaminomethylenebisphosphonate as a white powder (3.90 g, 43% ).

Workup

  1. temperaturethe mixture was refluxed for 2.5 hours
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure, water
  3. additionwas poured
  4. customseparated crystals
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-a566d50c9d614f70b479e26969f5c2a8
Source dataset
uspto-grants-1994_12
Patent number
US05376647

Reaction notes

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