Imidazole → HCID 19033237, compound

HRID 266606Notes

Reaction equation

HRID 266606 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([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27]1.N1C=CN=C1>>[CH:26]1([N:31]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])[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

4

Reactant 3

HCID 795ImidazoleHCID 2906CyclopentylamineHCID 11759069Perylene-3,4-dicarboxylic anhydride

Product 1

HCID 19033237HCID 19033237, compound

Conditions

Temperature
145 °C

Procedure

0.30 g (0.93 mmol) of perylene-3,4-dicarboxylic anhydride is mixed with 0.24 g (2.80 mmol) of cyclopentylamine and 3 g of imidazole, and the mixture is heated under nitrogen at 145° C. for 4 h. The reaction product is removed from the flask by washing with ethanol, and the mixture is then treated with 10% hydrochloric acid and boiled until no more ethanol is present. The precipitated product is filtered off with suction, boiled in potassium carbonate solution and the solid residue is filtered off with suction and washed with hot dist. water. 60 mg (20%) of perylene-3,4-dicarboxylic anhydride can be recovered by acidifying the filtrate with conc. hydrochloric acid. The red residue is recrystallized 3 times by extraction with methanol and then dried in a drying cabinet at 120° C. Yield 0.22 g (61%) of dark-red small needles showing a strong red solid fluorescence, m.p. >315° C. Rf (CHCl3 /silica gel)=0.18. UV (CHCl3): λmax (ε)=506 (31013), 485 (31425) 355 (3050), 336 (3000), 319 (2680), 264 (34268), 256 (sh., 18100). Fluorescence (CHCl3): λmax (Irel)=541 (1), 572 (sh., 0.49).

Workup

  1. customThe reaction product is removed from the flask
  2. washby washing with ethanol
  3. additionthe mixture is then treated with 10% hydrochloric acid
  4. filtrationThe precipitated product is filtered off with suction
  5. filtrationthe solid residue is filtered off with suction
  6. washwashed with hot dist
  7. custom60 mg (20%) of perylene-3,4-dicarboxylic anhydride can be recovered
  8. customThe red residue is recrystallized 3 times
  9. extractionby extraction with methanol
  10. customdried in a drying cabinet at 120° C

Sources & evidence

ORD record
ord-5234ab73cce84da4a5cbda64d0d108d1
Source dataset
uspto-grants-1997_07
Patent number
US05650513

Reaction notes

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