Bromotrimethylsilane → HCID 131718314, compound

HRID 1198126Notes

Reaction equation

HRID 1198126 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH2:5][NH:6][CH:7]([P:16](=[O:23])([O:20]CC)[O:17]CC)[P:8](=[O:15])([O:12]CC)[O:9]CC.Br[Si](C)(C)C>C(#N)C.O>[OH2:9].[CH3:1][S:2][CH2:3][CH2:4][CH2:5][NH:6][CH:7]([P:8](=[O:9])([OH:15])[OH:12])[P:16](=[O:17])([OH:20])[OH:23].[CH3:1][S:2][CH2:3][CH2:4][CH2:5][NH:6][CH:7]([P:8](=[O:9])([OH:15])[OH:12])[P:16](=[O:17])([OH:20])[OH:23]

Participants

5

Reactant 2

HCID 76113BromotrimethylsilaneHCID 53698278HCID 53698278, compound

Product 1

HCID 131718314HCID 131718314, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of tetraethyl 3-methylthiopropylaminomethylenebisphosphonate (5.28 g) in acetonitrile (100 ml) was added bromotrimethylsilane (12.39 g) and the mixture was stirred at room temperature for 15 hours. The reaction mixture was diluted with water (3.2 ml) and concentrated under reduced pressure. The solid residue was collected by filtration and recrystallized from water-methanol to give 3-methylthiopropylaminomethylenebisphosphonic acid hemihydrate (1.84 g, 47%). Colorless prisms, m.p. 120°-122° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. filtrationThe solid residue was collected by filtration
  3. customrecrystallized from water-methanol

Sources & evidence

ORD record
ord-ee2a13ea3073413a86771103c3639502
Source dataset
uspto-grants-1994_01
Patent number
US05280022

Reaction notes

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