Pyrrole → 5,10,15,20-Tetrakis(thiazol-5-yl)porphyrin

HRID 458081Notes

Reaction equation

HRID 458081 reaction equation
[S:1]1[C:5]([CH:6]=O)=[CH:4][N:3]=[CH:2]1.[NH:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1>C(O)(=O)CC>[S:1]1[C:5]([C:6]2[C:12]3[NH:8][C:9]([C:6]([C:5]4[S:1][CH:2]=[N:3][CH:4]=4)=[C:9]4[N:8]=[C:12]([C:6]([C:5]5[S:1][CH:2]=[N:3][CH:4]=5)=[C:9]5[NH:8][C:12](=[C:6]([C:5]6[S:1][CH:2]=[N:3][CH:4]=6)[C:9]6[CH:10]=[CH:11][C:12]=2[N:8]=6)[CH:11]=[CH:10]5)[CH:11]=[CH:10]4)=[CH:10][CH:11]=3)=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 8027PyrroleHCID 27735771,3-Thiazole-5-carbaldehyde

Product 1

HCID 1360825975,10,15,20-Tetrakis(thiazol-5-yl)porphyrinYield 23.2%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent2×

Procedure

A 250-mL three-necked flask equipped with a condenser and charged with propionic acid (60 mL) was heated to reflux. 5-Thiazolecarboxaldehyde (1,373 mg, 3.30 mmol), pyrrole (230 μL, 3.32 mmol), and an additional 5 mL of propionic acid were added. After 3.5 h at reflux, the mixture was cooled to room temperature while exposed to a stream of air. The solvent was removed in vacuo, the residue was redissolved in CHCl3/MeOH/concentrated NH4OH (6:3:1; 100 mL), and the solvent was removed in vacuo. The residue was adsorbed onto silica gel (3 g) and purified by column chromatography (gradient elution. 1–2% MeOH/CH2Cl2) to provide porphyrin 6 (123 mg, 14%) as a solid: 1H NMR (300 MHz, CDCl2) δ −2.70 (s, 2H), 8.67 (s, 4H), 9.02 (s, 8H), 9.38 (s, 4H).

Workup

  1. customA 250-mL three-necked flask equipped with a condenser
  2. temperaturewas heated to reflux
  3. temperatureAfter 3.5 h at reflux
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue was redissolved in CHCl3/MeOH/concentrated NH4OH (6:3:1; 100 mL)
  6. customthe solvent was removed in vacuo
  7. custompurified by column chromatography (gradient elution. 1–2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3d24fc6baddd43839be50d362457e332
Source dataset
uspto-grants-2007_03
Patent number
US07189707B2

Reaction notes

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