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

HRID 1939133Notes

Reaction equation

HRID 1939133 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 (D2O) 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-a8d0e344369c4aa7971b5f11b308fa2d
Source dataset
uspto-grants-1997_12
Patent number
US05695890

Reaction notes

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