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

HRID 1075683

反応式

HRID 1075683 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-7b3ce072d77347febec623f59e4a257b
出典データセット
uspto-grants-1999_05
特許番号
US05906892

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