Water → HCID 57865058, compound

HRID 886662Notes

Reaction equation

HRID 886662 reaction equation
N1N[N:3]=[N:4][C:5]=1[C:6]1[CH:19]=[CH:18][C:17]2[C:8](=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH:13]=[CH:12][CH:11]=[N:10]3)[N:7]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:26](Cl)(=[O:36])[C:27]1[CH:35]=[CH:34][CH:33]=[C:29]([C:30](Cl)=[O:31])[CH:28]=1.O>CCCCCC.CO.C(Cl)(Cl)Cl>[N:20]1[C:25]2[C:24](=[CH:15][CH:16]=[C:17]3[C:8]=2[N:7]=[CH:6][CH:19]=[CH:18]3)[CH:23]=[CH:22][C:21]=1[C:5]1[O:36][C:26]([C:27]2[CH:35]=[CH:34][CH:33]=[C:29]([C:30]3[O:31][C:5]([C:6]4[CH:19]=[CH:18][C:17]5[C:8](=[C:9]6[C:14](=[CH:15][CH:16]=5)[CH:13]=[CH:12][CH:11]=[N:10]6)[N:7]=4)=[N:4][N:3]=3)[CH:28]=2)=[N:3][N:4]=1

Participants

8

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7451Isophthaloyl chlorideHCID 58979972HCID 58979972, compound

Product 1

HCID 57865058HCID 57865058, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

After dissolving 5.0 g of 2-(2H-tetrazole-5-yl)-1,10-phenanthroline into 50 ml of dehydrated pyridine, 2.1 g of isophthaloylchloride was added. The mixture was heated to 100° C. and stirred under reflux for 5 hours. After cooling to a room temperature, the reaction solution was poured into water to collect a precipitated solid by suction filtration, and the solid was washed with water. The solid was dried under vacuum at 70° C. for 20 hours to obtain a brownish crude product. After dissolving the thus-obtained crude product into a mixed solution of chloroform:methanol=4:1, hexane was added to allow purification by crystallization, thereby obtaining 4.82 g of PhenOXDm (2) (yield: 84%). NMR analysis (see FIG. 1) was performed for identification of the product. The results of the NMR analysis are as follows. 9.15 ppm (2H), 8.89 ppm (1H), 8.73 ppm (2H), 8.59 ppm (2H), 8.50 ppm (2H), 8.45 ppm (2H), 8.07 ppm (4H), 7.97 ppm (1H), 7.78 ppm (2H).

Workup

  1. additionwas added
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling to a room temperature
  4. customto collect a precipitated solid
  5. filtrationby suction filtration
  6. washthe solid was washed with water
  7. customThe solid was dried under vacuum at 70° C. for 20 hours
  8. customto obtain a brownish crude product
  9. dissolutionAfter dissolving the
  10. custompurification
  11. customby crystallization

Sources & evidence

ORD record
ord-4ba72352171a4ba1832a35c72f1ad41f
Source dataset
uspto-grants-2012_08
Patent number
US08247087B2

Reaction notes

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