3-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene → Phthalocyanine

HRID 1488904Notes

Reaction equation

HRID 1488904 reaction equation
[NH:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[NH:11])[NH:3]1.C1(C2CCCCCCCCCC=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][NH:14]N=1>[Ni](Cl)Cl.CO>[CH:8]1[CH:7]=[CH:6][C:5]2[C:10](=[C:2]3[N:1]=[C:15]4[N:14]=[C:22]([C:21]5[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=54)[N:11]=[C:4]4[NH:3][C:2]([C:10]5[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=54)=[N:1][C:15]4=[N:14][C:22]([C:21]5[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=54)=[N:11][C:4]=2[NH:3]3)[CH:9]=1

Participants

5

Reactant 2

HCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-eneHCID 178508669HCID 178508669, compound

Product 1

HCID 86280045PhthalocyanineYield 28.5%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

In 20 g of n-amylalcohol were dissolved 10 g (0.02865 mole) of the diiminoisoindoline of the formula (XXXII) and 4.36 g (0.02863 mole) of diazabicycloundecene, to which 0.92 g (0.0071 mole) of nickel chloride was added. The mixture was then heated under reflux for 30 hours. The reaction mixture was then cooled to room temperature and poured into 120 ml of methanol. The crystals thus precipitated were washed with a small amount of methanol and the resulting crystals were purified with a chloroform/THF (=9/1 (weight ratio))/silica gel column to obtain 2.1 g (yield: 25.2%) of a phthalocyanine compound of the formula (XXIII) below. This compound showed max in toluene of 749 nm and logC- of 5.10. The IR spectrum of this compound is shown in FIG. 9. ##STR54##

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 30 hours
  3. customThe crystals thus precipitated
  4. washwere washed with a small amount of methanol
  5. customthe resulting crystals were purified with a chloroform/THF (=9/1 (weight ratio))/silica gel column

Sources & evidence

ORD record
ord-0ef16968c5984277aa8686bcd5b92dc8
Source dataset
uspto-grants-1997_10
Patent number
US05677025

Reaction notes

Loading…