Imidazole → N-(1-Octylnonyl)perylene-3,4-dicarboximide

HRID 266599

Reaction equation

HRID 266599 reaction equation
[CH:1]1[C:10]2[C:11]3[CH:20]=[CH:19][C:18]4[C:21]([O:23][C:24](=O)[C:16]5[C:17]=4[C:12]=3[C:13](=[CH:14][CH:15]=5)[C:8]3[C:9]=2[C:4]2[C:5](C(OC(=O)[C:3]=2[CH:2]=1)=O)=[CH:6][CH:7]=3)=[O:22].N1C=CN=C1.[NH2:36][CH:37]([CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45].O.C(C1C=CC(C(C)(C)C)=CC=1N1C(=O)C2C3C4C(=CC=2)C2C5C(C=CC=2)=CC=CC=5C=4C=CC=3C1=O)(C)(C)C>O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[CH2:38]([CH:37]([N:36]1[C:21](=[O:22])[C:18]2[C:17]3[C:12]4[C:11](=[CH:20][CH:19]=2)[C:10]2[C:9]5[C:4]([CH:3]=[CH:2][CH:1]=2)=[CH:5][CH:6]=[CH:7][C:8]=5[C:13]=4[CH:14]=[CH:15][C:16]=3[C:24]1=[O:23])[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]

Participants

7

Reactant 5

HCID 795ImidazoleHCID 962WaterHCID 671913,4,9,10-Perylenetetracarboxylic dianhydrideHCID 408570Heptadecan-9-amineHCID 11081772HCID 11081772, compound

Product 1

HCID 19033227N-(1-Octylnonyl)perylene-3,4-dicarboximide

Reagents, catalysts & solvents 1

HCID 2724192Zinc acetate (USP)Catalyst

Procedure

1.4 g (3.1 mmol) of perylene-3,4,9,10-tetracarboxylic dianhydride, 6.1 g of imidazole, 960 mg (3.7 mmol) of 9-aminoheptadecane (prepared according to DE-A 4,007,618), 150 mg (0.68 mmol) of zinc acetate dihydrate and 3.0 ml (170 mmol) of water are heated in an autoclave (100 ml) at 190° C. for 24 h. Workup is analogous to that used for preparing 2b. Yield 130 mg (7% by extractive recrystallization from methanol, such as described in Chem. Ber. 1985, 118, 4641) orange red crystals showing strong solid fluorescence, m.p. 143°-143.6° C. Rf (CHCl3 /silica gel)=0.94. UV (CHCl3): λmax (ε)=454 nm (sh, 17620), 485 (32530), 508 (29480). Fluorescence (CHCl3, exc. 485 nm): λmax (Irel)=572 (sh, 0.49), 536 (1).

Workup

  1. customYield 130 mg (7% by extractive recrystallization from methanol, such as described in Chem. Ber. 1985, 118, 4641) orange red crystals

Sources & evidence

ORD record
ord-b148e3223a964806845bb601e8e248b0
Source dataset
uspto-grants-1997_07
Patent number
US05650513

Linked notes

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