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

HRID 635427

반응식

HRID 635427 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.)

후처리

  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

출처 및 근거

ORD 기록
ord-89e50e04455d484598128abce3451760
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06187871B1

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