Water → 6,6'-[1,3-Phenylenedi(1,3,4-oxadiazole-5,2-diyl)]di(2,2'-bipyridine)

HRID 1012590Notes

Reaction equation

HRID 1012590 reaction equation
N1N[N:3]=[N:4][C:5]=1[C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:9]=[CH:8][CH:7]=1.[C:18](Cl)(=[O:28])[C:19]1[CH:27]=[CH:26][CH:25]=[C:21]([C:22](Cl)=[O:23])[CH:20]=1.O>N1C=CC=CC=1>[N:11]1[C:6]([C:5]2[O:28][C:18]([C:19]3[CH:27]=[CH:26][CH:25]=[C:21]([C:22]4[O:23][C:5]([C:6]5[N:11]=[C:10]([C:12]6[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=6)[CH:9]=[CH:8][CH:7]=5)=[N:4][N:3]=4)[CH:20]=3)=[N:3][N:4]=2)=[CH:7][CH:8]=[CH:9][C:10]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7451Isophthaloyl chlorideHCID 573549016-(2H-Tetrazol-5-yl)-2,2'-bipyridine

Product 1

HCID 593364626,6'-[1,3-Phenylenedi(1,3,4-oxadiazole-5,2-diyl)]di(2,2'-bipyridine)Yield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.63 g of 6-(2H-tetrazol-5-yl)-2,2′-bipyridine was dissolved in 10 ml of dehydrated pyridine, and 0.29 g of isophthaloyl dichloride was gradually added. Temperature was elevated to 115° C., and stirring was conducted for 6 hours under reflux. After cooling to room temperature, the reaction solution was poured into water, and a precipitated white solid was taken out by suction filtration, and washed with water. The solid obtained was vacuum dried at 80° C. for 20 hours, and purified with column chromatography (carrier: silica gel, eluting solution: chloroform/methanol=20/1) to obtain 0.62 g (yield 81%) of BpyOXDm. The product was identified with NMR analysis. The result of NMR analysis (CDCl3) was as follows. 9.071 ppm (1H), 8.639-8.714 ppm (6H), 8.325-8.477 ppm (4H), 8.037 ppm (2H), 7.756-7.854 ppm (3H), 7.330 ppm (2H).

Workup

  1. customwas elevated to 115° C.
  2. temperatureunder reflux
  3. filtrationa precipitated white solid was taken out by suction filtration
  4. washwashed with water
  5. customThe solid obtained
  6. customdried at 80° C. for 20 hours
  7. custompurified with column chromatography (carrier: silica gel, eluting solution: chloroform/methanol=20/1)
  8. customto obtain 0.62 g (yield 81%) of BpyOXDm
  9. customThe result of NMR analysis (CDCl3)

Sources & evidence

ORD record
ord-4e8b9a7b1c9c4f2496986fc5b03ac8b9
Source dataset
uspto-grants-2011_07
Patent number
US07977671B2

Reaction notes

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