Toluene → [2,3-Quinoxalindiyl]bis(methylene) bisphosphonic acid tetramethyl ester

HRID 2379025

Reaction equation

HRID 2379025 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6]C=C[CH:9]=2)[N:4]=CC=1.C[O:12][P:13]([O:16][CH3:17])[O:14][CH3:15].[C:18]1(C)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH3:15][O:14][P:13]([CH2:6][C:5]1[C:10]([CH2:9][P:13](=[O:12])([O:16][CH3:17])[O:14][CH3:15])=[N:1][C:18]2[C:19]([N:4]=1)=[CH:20][CH:21]=[CH:22][CH:23]=2)(=[O:12])[O:16][CH3:17]

Participants

4

Reactant 3

HCID 1140TolueneHCID 7045QuinoxalineHCID 8472Trimethyl phosphite

Product 1

HCID 86747692[2,3-Quinoxalindiyl]bis(methylene) bisphosphonic acid tetramethyl ester

Procedure

This known compound is prepared by making a solution of quinoxaline (3.16 g, 10 mmol) in hot toluene (20 ml) and treating with trimethylphosphite (2.73 g, 22 mmol). The mixture is heated at reflux temperature for 24 hours. The cooled solution deposits [2,3-quinoxalindiyl]bis(methylene) bisphosphonic acid tetramethyl ester (2.70 g, m.p. 113°-114° C.) after recrystallization from toluene. V. A. Arbuzov et al. Izvest Acad. Nauk SSSR, 1961, 1016; 1954, E 868; (Chem Abstracts (CA) 55:27352b; CA 49:13222e) report a m.p. 115°-116° C.

Workup

  1. customThis known compound is prepared
  2. temperatureThe mixture is heated
  3. temperatureat reflux temperature for 24 hours
  4. customThe cooled solution deposits [2,3-quinoxalindiyl]bis(methylene) bisphosphonic acid tetramethyl ester (2.70 g, m.p. 113°-114° C.) after recrystallization from toluene

Sources & evidence

ORD record
ord-f34d2c28a3e748239ebc0e43af627408
Source dataset
uspto-grants-1994_11
Patent number
US05360797

Linked notes

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