Hydrochloric Acid → HCID 19033222, compound

HRID 266605

Reaction equation

HRID 266605 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].[C:26]([C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1)([CH3:29])([CH3:28])[CH3:27].N1C=CN=C1.Cl>O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C.C(O)C>[C:26]([C:30]1[CH:31]=[CH:32][C:33]([N:34]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])=[CH:35][CH:36]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 698614-Tert-ButylanilineHCID 11759069Perylene-3,4-dicarboxylic anhydride

Product 1

HCID 19033222HCID 19033222, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 2724192Zinc acetate (USP)CatalystHCID 702EthanolSolvent2×

Procedure

0.70 g (2.17 mmol) of perylene-3,4-dicarboxylic anhydride is mixed with 0.49 g (3.28 mmol) of 4-t-butylaniline, 3.00 g of imidazole and 0.10 g of zinc acetate dihydrate and the mixture is heated at 140°-150° C. for 5 h. While still hot, the mixture is treated with 100 ml of ethanol, and then 200 ml of 10% hydrochloric acid are added. The red suspension is heated until all the ethanol has evaporated, and the product is then filtered off with suction. The red-brown residue is boiled in 10% potassium carbonate solution, the solid residue is filtered off with suction while hot and rinsed several times with hot dist. water. The red residue is dried in a drying cabinet at 120° C. and then recrystallized by extraction with a toluene/methanol mixture to give 0.80 g (81%) of red N-(4-t-butylphenyl)perylene-3,4-dicarboximide which shows a red solid fluorescence. M.p. >330° C. Rf (CHCl3 /silica gel)=0.35.

Workup

  1. temperaturethe mixture is heated at 140°-150° C. for 5 h
  2. customhas evaporated
  3. filtrationthe product is then filtered off with suction
  4. filtrationthe solid residue is filtered off with suction while hot and
  5. washrinsed several times with hot dist
  6. customThe red residue is dried in a drying cabinet at 120° C.
  7. customrecrystallized by extraction with a toluene/methanol mixture

Sources & evidence

ORD record
ord-16dd334854764a0590178515dbeeb052
Source dataset
uspto-grants-1997_07
Patent number
US05650513

Linked notes

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