Imidazole → HCID 19033234, compound

HRID 266608Notes

Reaction equation

HRID 266608 reaction equation
[CH:1]1[C:18]2=[C:19]3[C:8]([C:9]4[C:20]5[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=5)[CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[C:5]2[C:21]([O:23][C:24](=O)[C:3](=[C:4]23)[CH:2]=1)=[O:22].[CH:26]1([NH2:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.N1C=CN=C1>>[CH:26]1([N:33]2[C:21](=[O:22])[C:5]3[C:4]4[C:19]5[C:8](=[CH:7][CH:6]=3)[C:9]3[C:20]6[C:13]([CH:12]=[CH:11][CH:10]=3)=[CH:14][CH:15]=[CH:16][C:17]=6[C:18]=5[CH:1]=[CH:2][C:3]=4[C:24]2=[O:23])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

4

Reactant 3

HCID 795ImidazoleHCID 2899CycloheptylamineHCID 11759069Perylene-3,4-dicarboxylic anhydride

Product 1

HCID 19033234HCID 19033234, compound

Conditions

Temperature
150 °C

Procedure

0.30 g (0.93 mmol) of perylene-3,4-dicarboxylic anhydride is mixed with 0.32 g (2.83 mmol) of cycloheptylamine and 3 g of imidazole, and the mixture is heated under argon at 150° C. for 4 h. The reaction product is removed from the flask by washing with ethanol, treated with 200 ml of 10% hydrochloric acid and filtered off with suction. The residue is boiled in potassium carbonate solution, filtered off with suction and washed with hot dist. water until the filtrate run-off is colourless. The product thus obtained is dried in a drying cabinet at 120° C. and then recrystallized by extraction with methanol. Yield 0.24 g (62%) of orange crystals showing a red solid fluorescence, m.p. 354°-355° C., Rf (CHCl3 /silica gel)=0.79. UV (CHCl3): λmax (ε)=505 (30370), 483 (30967), 353 (3170), 336 (3170), 295 (3460), 264 (29047). Fluorescence (CHCl3): λmax (Irel)=529 (1), 568 (0.48).

Workup

  1. customThe reaction product is removed from the flask
  2. washby washing with ethanol
  3. additiontreated with 200 ml of 10% hydrochloric acid
  4. filtrationfiltered off with suction
  5. filtrationfiltered off with suction
  6. washwashed with hot dist
  7. customThe product thus obtained
  8. customis dried in a drying cabinet at 120° C.
  9. customrecrystallized by extraction with methanol

Sources & evidence

ORD record
ord-efcc892ccb714c7f89eb99607164e449
Source dataset
uspto-grants-1997_07
Patent number
US05650513

Reaction notes

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