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

HRID 266598

Reaction equation

HRID 266598 reaction equation
[CH:1]1[C:10]2[C:11]3[CH:20]=[CH:19][C:18]4C(OC(=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:26](O[C:29](=[O:30])[C:3]=2[CH:2]=1)=[O:27])=[CH:6][CH:7]=3)=O.N1C=CN=C1.[NH2:36][CH:37]([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].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:26](=[O:27])[C:5]2[C:4]3[C:9]4[C:8](=[CH:7][CH:6]=2)[C:13]2[C:12]5[C:17]([CH:16]=[CH:15][CH:14]=2)=[CH:18][CH:19]=[CH:20][C:11]=5[C:10]=4[CH:1]=[CH:2][C:3]=3[C:29]1=[O:30])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

Participants

7

Reactant 5

HCID 795ImidazoleHCID 962WaterHCID 671913,4,9,10-Perylenetetracarboxylic dianhydrideHCID 574991Tridecan-7-amineHCID 11081772HCID 11081772, compound

Product 1

HCID 11443487N-(1-Hexylheptyl)perylene-3,4-dicarboximide

Reagents, catalysts & solvents 1

HCID 2724192Zinc acetate (USP)Catalyst

Procedure

1.2 g (3.1 mmol) of perylene-3,4,9, 10-tetracarboxylic dianhydride, 6.2 g of imidazole, 470 mg (2.36 mmol) of 7-aminotridecane (prepared according to J. Prakt. Chem. 1980, 322, 261), 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 in the preparation of 2b. Yield 1.25 g (27%).

Sources & evidence

ORD record
ord-67282756a1ef482bb6fc7c4ab8f27489
Source dataset
uspto-grants-1997_07
Patent number
US05650513

Linked notes

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