Imidazole → HCID 15476509, compound

HRID 266607Notes

Reaction equation

HRID 266607 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([NH2:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.N1C=CN=C1>>[CH:26]1([N:32]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])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

4

Reactant 3

HCID 795ImidazoleHCID 7965CyclohexylamineHCID 11759069Perylene-3,4-dicarboxylic anhydride

Product 1

HCID 15476509HCID 15476509, compound

Conditions

Temperature
140 °C

Procedure

0.30 g (0.93 mmol) of perylene-3,4-dicarboxylic anhydride is mixed with 0.28 g (2.8 mmol) of cyclohexylamine and 3 g of imidazole, and the mixture is heated under nitrogen at 140° C. for 3 h. The reaction product is removed from the flask by washing with ethanol, treated with 200 ml of 10% hydrochloric acid and boiled until no more ethanol is present. The residue is filtered off with suction, boiled in potassium carbonate solution and again filtered off with suction. The residue is washed with hot water until the filtrate is hardly coloured any more and then dried in a drying cabinet at 120° C. The orange shiny powder thus obtained is recrystallized twice by extraction with methanol. Yield 0.30 g (80%) of orange small crystals, strong red solid fluorescence, m.p. 370°-372° C. Rf (CHCl3 /silica gel)=0.41. UV (CHCl3): λmax (ε)=505 (29970), 483 (30309), 354 (3160), 336 (3160), 294 (3300), 264 (29090). Fluorescence (CHCl3): λmax (Irel)=539 (1), 567 (0.51).

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. filtrationThe residue is filtered off with suction
  5. filtrationagain filtered off with suction
  6. washThe residue is washed with hot water until the filtrate
  7. customthen dried in a drying cabinet at 120° C
  8. customThe orange shiny powder thus obtained
  9. customis recrystallized twice by extraction with methanol

Sources & evidence

ORD record
ord-bf839be530d24192823a399da86319de
Source dataset
uspto-grants-1997_07
Patent number
US05650513

Reaction notes

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