Imidazole → N-Cyclododecylperylene-3,4-dicarboximide

HRID 266603Notes

Reaction equation

HRID 266603 reaction equation
C1C2=C3C(C4C5C(=CC=CC2=5)C=CC=4)=CC=C2C(OC(=O)C(=C23)C=1)=O.C1(N)CCCCCCCCCCC1.N1C=CN=C1.[CH2:44]([CH:50]([N:57]1[C:79](=[O:80])[C:76]2[C:77]3[C:78]4[C:73](=[CH:74][CH:75]=2)[C:72]2[C:81]5[C:68]([CH:69]=[CH:70][CH:71]=2)=[CH:67][CH:66]=[CH:65][C:64]=5[C:63]=4[CH:62]=[CH:61][C:60]=3[C:58]1=[O:59])[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55]C)[CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]>C(Cl)(Cl)Cl>[CH:50]1([N:57]2[C:58](=[O:59])[C:60]3[C:77]4[C:78]5[C:63](=[CH:62][CH:61]=3)[C:64]3[C:81]6[C:68]([CH:67]=[CH:66][CH:65]=3)=[CH:69][CH:70]=[CH:71][C:72]=6[C:73]=5[CH:74]=[CH:75][C:76]=4[C:79]2=[O:80])[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 2897CyclododecanamineHCID 11443487N-(1-Hexylheptyl)perylene-3,4-dicarboximideHCID 11759069Perylene-3,4-dicarboxylic anhydride

Product 1

HCID 19033238N-Cyclododecylperylene-3,4-dicarboximide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

190 mg (0.56 mmol) of perylene-3,4-dicarboxylic anhydride are reacted with 140 mg (1.28 mmol) of cyclododecylamine and 2.0 g of imidazole under an argon inert atmosphere as in 2c, and the reaction product is worked up. After chromatography on silica gel using chloroform, it is recrystallized by extraction with toluene. Yield 190 mg (66%), m.p. 285° C., Rf (CHCl3 /silica gel)=0.58. UV (CHCl3): λmax (ε): 454 (shoulder, 19085), 484 (32630), 507 (32015). Fluorescence (CHCl3, exc. 584 nm) λmax (Irel)=538 (1), 572 (sh, 0.44).

Workup

  1. customis recrystallized by extraction with toluene

Sources & evidence

ORD record
ord-03b934d9077a4d16a7cfc0328aa65356
Source dataset
uspto-grants-1997_07
Patent number
US05650513

Reaction notes

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