Water → HCID 59236801, compound

HRID 1159748Notes

Reaction equation

HRID 1159748 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:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O.[OH-].[Na+]>N1C=CC=CC=1>[C:19]1([C:18]2[O:25][C:13]([C:9]3[N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:12]=[CH:11][CH:10]=3)=[N:14][N:15]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 67315018HCID 67315018, compound

Product 1

HCID 59236801HCID 59236801, compoundYield 91%

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., 3.17 g of benzoyl chloride was added. Temperature was elevated to 100° C., and stirring was conducted for 2 hours under flux. 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 yellow 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 adsorption purification (carrier: NH silica gel, eluting solution: chloroform) to obtain 6.11 g (yield 91%) of PhpyOXDPh. The product was identified with NMR analysis. The result of NMR analysis (CDCl3) was as follows. 8.23-8.26 ppm (3H), 8.14-8.17 ppm (2H), 7.90-7.99 ppm (2H), 7.48-7.58 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 yellow 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 adsorption purification (carrier: NH silica gel, eluting solution: chloroform)
  11. customto obtain 6.11 g (yield 91%) of PhpyOXDPh
  12. customThe result of NMR analysis (CDCl3)

Sources & evidence

ORD record
ord-b6217d15a9e2429fb5bb1836bfa05b57
Source dataset
uspto-grants-2010_10
Patent number
US07812341B2

Reaction notes

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