Water → HCID 59236811, compound

HRID 1012594Notes

Reaction equation

HRID 1012594 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[N:14]=[N:15]NN=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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.[OH-].[Na+]>N1C=CC=CC=1>[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[O:28][C:18]([C:19]4[CH:27]=[CH:26][CH:25]=[C:21]([C:22]5[O:23][C:13]([C:9]6[N:8]=[C:7]([C:1]7[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=7)[CH:12]=[CH:11][CH:10]=6)=[N:14][N:15]=5)[CH:20]=4)=[N:15][N:14]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7451Isophthaloyl chlorideHCID 14798Sodium HydroxideHCID 67315018HCID 67315018, compound

Product 1

HCID 59236811HCID 59236811, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

5.0 g of 2-phenyl-6-(2H-tetrazol-5-yl)pyridine was dissolved in 125 ml of dehydrated pyridine. Temperature was elevated to 120° C., and 75 ml was dehydrated by azeotropy. After cooling to 50° C., 2.28 g of isophthaloyl dichloride was added. Temperature was elevated to 100° C., and stirring was conducted for 1 hour. After cooling to room temperature, the reaction solution was poured into 300 ml water, and after adjusting pH to 12 with 20% sodium hydroxide aqueous solution, stirring was conducted for 1 hour. A precipitated brown solid was taken out by suction filtration, and washed with water. The solid obtained was vacuum dried at 70° C. for 20 hours, and purified with column chromatography (carrier: NH silica gel, eluting solution: chloroform) to obtain 4.27 g (yield 73%) of PhpyOXDm. The product was identified with NMR analysis. The result of NMR analysis (CDCl3) was as follows. 9.07 ppm (1H), 8.46 ppm (2H), 8.28 ppm (2H), 8.17 ppm (4H), 7.92-8.15 ppm (4H), 7.78 ppm (1H), 7.46-7.55 ppm (6H).

Workup

  1. customwas elevated to 120° C.
  2. customwas elevated to 100° C.
  3. temperatureAfter cooling to room temperature
  4. stirringstirring
  5. waitwas conducted for 1 hour
  6. filtrationA precipitated brown solid was taken out by suction filtration
  7. washwashed with water
  8. customThe solid obtained
  9. customdried at 70° C. for 20 hours
  10. custompurified with column chromatography (carrier: NH silica gel, eluting solution: chloroform)
  11. customto obtain 4.27 g (yield 73%) of PhpyOXDm
  12. customThe result of NMR analysis (CDCl3)

Sources & evidence

ORD record
ord-28005ac25c8247c59218e02eadb8dd83
Source dataset
uspto-grants-2011_07
Patent number
US07977671B2

Reaction notes

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