Water → 1287-16-7

HRID 2185089Notes

Reaction equation

HRID 2185089 reaction equation
[C-:1]1([CH2:6][C:7](Cl)=[O:8])[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.[Fe+2:15].N1C=CC=CC=1.[OH2:22]>CN(C)C1C=CN=CC=1>[C-:1]1([CH2:6][C:7]([OH:8])=[O:22])[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.[Fe+2:15]

Participants

5

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 178521134HCID 178521134, compound

Product 1

HCID 157685011287-16-7

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A 50 ml round-bottom flask, equipped with magnetic stirrer and nitrogen inlet, is charged with 0.50 g (0.19 mmol) of ferrocene acetic acid chloride (prepared in analogy to a process slightly modified from Macromolecules 26 (1993) 1936-1940), 10 ml of pyridine, 1.28 g (0.95 mmol) of brominated and, hydroxymethylated tetra(α-2,4-dimethyl-3-pentyloxy)palladium-phthalocyanine and 12 mg (0.1 mmol) of 4-dimethylaminopyridine under argon, and the dark green solution is stirred for 20 hours at room temperature. The reaction mixture is then poured, with thorough stirring, on 100 ml of water and the precipitate is collected by filtration and washed with 4×50 ml of water. After drying the residue for 4 hours at 60° C. and 125 torr, it is dissolved in 15 ml of toluene and then 1.3 g of silica gel are added and the mixture is stirred for 10 minutes. The suspension is filtered and the residue is washed with 3×10 ml of toluene. Using a rotary evaporator, the filtrate is concentrated by evaporation to 4.8 g of a solution which is then poured, with stirring, on 49 ml of acetonitrile and stirred for 10 minutes. The precipitate is collected by filtration, washed with 3×50 ml of acetonitrile and dried overnight at 60° C. and 125 torr, yielding 1.2 g (80.5% of theory) of a green powder (brominated and hydroxymethylated tetra(α-2,4-dimethyl-3-pentyloxy)palladium-phthalocyanine which is esterified with ferrocene acetic acid) having the following analytical values:

Workup

  1. customA 50 ml round-bottom flask, equipped with magnetic stirrer and nitrogen inlet
  2. customprepared in analogy to a process
  3. filtrationthe precipitate is collected by filtration
  4. washwashed with 4×50 ml of water
  5. customAfter drying the residue for 4 hours at 60° C.
  6. dissolution125 torr, it is dissolved in 15 ml of toluene
  7. addition1.3 g of silica gel are added
  8. filtrationThe suspension is filtered
  9. washthe residue is washed with 3×10 ml of toluene
  10. customa rotary evaporator
  11. concentrationthe filtrate is concentrated by evaporation to 4.8 g of a solution which
  12. additionis then poured
  13. stirringwith stirring, on 49 ml of acetonitrile
  14. stirringstirred for 10 minutes
  15. filtrationThe precipitate is collected by filtration
  16. washwashed with 3×50 ml of acetonitrile
  17. customdried overnight at 60° C.

Sources & evidence

ORD record
ord-a14041f540514368a511b77f02ff9972
Source dataset
uspto-grants-2002_06
Patent number
US06399768B1

Reaction notes

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