Water → HCID 59236812, compound

HRID 1012592Notes

Reaction equation

HRID 1012592 reaction equation
[N:1]1[NH:2]N=N[C:5]=1[C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[N:13]=2)[CH:9]=[CH:8][CH:7]=1.[C:24](Cl)(=[O:34])[C:25]1[CH:33]=[CH:32][CH:31]=[C:27]([C:28](Cl)=[O:29])[CH:26]=1.O>N1C=CC=CC=1>[N:11]1[C:6]([C:5]2[O:34][C:24]([C:25]3[CH:33]=[CH:32][CH:31]=[C:27]([C:28]4[O:29][C:5]([C:6]5[N:11]=[C:10]([C:12]6[CH:17]=[CH:16][CH:15]=[C:14]([C:18]7[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=7)[N:13]=6)[CH:9]=[CH:8][CH:7]=5)=[N:1][N:2]=4)[CH:26]=3)=[N:2][N:1]=2)=[CH:7][CH:8]=[CH:9][C:10]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7451Isophthaloyl chlorideHCID 67315563HCID 67315563, compound

Product 1

HCID 59236812HCID 59236812, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

2.0 g of 6-(2H-tetrazol-5-yl)-2,2′:6′2″-terpyridine was dissolved in 50 ml of dehydrated pyridine. Temperature was elevated to 120° C., and 30 ml was dehydrated by azeotropy. After cooling to 50° C., 0.68 g of isophthaloyl dichloride was added. Temperature was elevated to 110° C., and stirring was conducted for 3 hours under flux. After cooling to room temperature, the reaction solution was poured into 200 ml water, and a precipitated yellowish-brown 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 adsorption purification (carrier: NH silica gel, eluting solution: chloroform) to obtain 1.53 g (yield 67%) of TpyOXDm. The product was identified with NMR analysis. The result of NMR analysis (CDCl3) was as follows. 9.12 ppm (1H), 8.85 ppm (2H), 8.62-8.73 ppm (6H), 8.37-8.51 ppm (6H), 7.79-8.12 ppm (7H), 7.35 ppm (2H).

Workup

  1. customwas elevated to 120° C.
  2. customwas elevated to 110° C.
  3. temperatureAfter cooling to room temperature
  4. filtrationa precipitated yellowish-brown solid was taken out by suction filtration
  5. washwashed with water
  6. customThe solid obtained
  7. customdried at 80° C. for 20 hours
  8. custompurified with adsorption purification (carrier: NH silica gel, eluting solution: chloroform)
  9. customto obtain 1.53 g (yield 67%) of TpyOXDm
  10. customThe result of NMR analysis (CDCl3)

Sources & evidence

ORD record
ord-f91282ee3be844ff938bf9361c75aa27
Source dataset
uspto-grants-2011_07
Patent number
US07977671B2

Reaction notes

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