Water → HCID 59236802, compound

HRID 1012591Notes

Reaction equation

HRID 1012591 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][C:22]([C:23](Cl)=[O:24])=[CH:21][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][C:22]([C:23]4[O:24][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:21][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 7488Terephthaloyl chlorideHCID 573549016-(2H-Tetrazol-5-yl)-2,2'-bipyridine

Product 1

HCID 59236802HCID 59236802, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.67 g of 6-(2H-tetrazol-5-yl)-2,2′-bipyridine was dissolved in 10 ml of dehydrated pyridine, and 0.32 g of terephthaloyl dichloride was added. Temperature was elevated to 110° C., and stirring was conducted for 5 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 was vacuum dried at 80° C. for 20 hours to obtain a while crude product. By purifying with column chromatography, 0.58 g (yield 74%) of BpyOXDp was obtained. The product was identified with NMR analysis. The result of NMR analysis (CDCl3) was as follows. 8.736 ppm (2H), 8.640 ppm (4H), 8.463 ppm (3H), 8.260-8.384 ppm (4H), 8.060 ppm (2H), 7.932 ppm (2H), 7.380 ppm (1H).

Workup

  1. customwas elevated to 110° C.
  2. temperatureunder reflux
  3. filtrationa precipitated white solid was taken out by suction filtration
  4. washwashed with water
  5. customdried at 80° C. for 20 hours
  6. customto obtain a while crude product
  7. customBy purifying with column chromatography, 0.58 g (yield 74%) of BpyOXDp
  8. customwas obtained
  9. customThe result of NMR analysis (CDCl3)

Sources & evidence

ORD record
ord-df69b8c08fc440e3baa2197adc87468e
Source dataset
uspto-grants-2011_07
Patent number
US07977671B2

Reaction notes

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