Hydrochloric Acid → 1,1'-Bis(2-phosphonoethyl)-[4,4'-bipyridine]-1,1'-diium chloride

HRID 1075683

Reaction equation

HRID 1075683 reaction equation
Br[CH2:2][CH2:3][P:4](=[O:11])([O:8]CC)[O:5]CC.[N:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1.[ClH:24]>O>[Cl-:24].[Cl-:24].[P:4]([CH2:3][CH2:2][N+:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][N+:21]([CH2:2][CH2:3][P:4]([OH:5])([OH:8])=[O:11])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)([OH:11])([OH:8])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 111074,4'-BipyridineHCID 79218Diethyl (2-bromoethyl)phosphonate

Product 1

HCID 149679671,1'-Bis(2-phosphonoethyl)-[4,4'-bipyridine]-1,1'-diium chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diethyl 2-bromoethylphosphonate (25 g) and 4,4' bipyridine (7.35 g) in 125 mls of water are refluxed for three days. An equal volume of concentrated hydrochloric acid is added and reflux continued for several hours. The solution is concentrated to 120 mls by atmospheric distillation and 550 mL of isopropanol are added dropwise with stirring while chilling the mixture in an ice bath. The solid which forms is collected by vacuum filtration and washed with cold isopropanol to yield 1,1'-bisphosphonoethyl-4,4'-bipyridinium dichloride. (1H NMR (D2) 9.1(d), 8.5(d), 4.2(m), 2.0(m) ppm; 13C NMR(D2O) 151, 147, 128, 58, 30 ppm; 31P NMR(D2O) 17.8 (s) ppm; IR (KBr) 3112, 3014, 1640, 1555, 1506, 1443, 1358, 1281, 1175, 1112, 1020, 936, 816, 485 cm-1)

Workup

  1. temperaturereflux
  2. waitcontinued for several hours
  3. concentrationThe solution is concentrated to 120 mls by atmospheric distillation and 550 mL of isopropanol
  4. additionare added dropwise
  5. temperaturewhile chilling the mixture in an ice bath
  6. filtrationThe solid which forms is collected by vacuum filtration
  7. washwashed with cold isopropanol

Sources & evidence

ORD record
ord-7b3ce072d77347febec623f59e4a257b
Source dataset
uspto-grants-1999_05
Patent number
US05906892

Linked notes

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