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

HRID 266601Notes

Reaction equation

HRID 266601 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].[NH2:26][CH:27]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].N1C=CN=C1.C(C(N1C(=O)C2C3C4C(=CC=2)C2C5C(C=CC=2)=CC=CC=5C=4C=CC=3C1=O)CCCCCC)CCCCC>C(Cl)(Cl)Cl>[CH2:28]([CH:27]([N:26]1[C:24](=[O:23])[C:3]2[C:4]3[C:19]4[C:18](=[CH:1][CH:2]=2)[C:17]2[C:20]5[C:13]([CH:14]=[CH:15][CH:16]=2)=[CH:12][CH:11]=[CH:10][C:9]=5[C:8]=4[CH:7]=[CH:6][C:5]=3[C:21]1=[O:22])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 76728Nonadecan-10-amineHCID 11443487N-(1-Hexylheptyl)perylene-3,4-dicarboximideHCID 11759069Perylene-3,4-dicarboxylic anhydride

Product 1

HCID 19033233N-(1-Nonyldecyl)perylene-3,4-dicarboximide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

230 mg (0.70 mmol) of perylene-3,4-dicarboxylic anhydride are reacted with 400 mg (1.40 mmol) of 10-aminononadecane (prepared according to DE-A 4,007,618) and 1.0 g of imidazole under an argon inert atmosphere as in 2c, followed by workup. After chromatography on silica gel using chloroform, the reaction product is applied to silica gel using petroleum ether, and the purely aliphatic by-products are washed off with about 11 of petroleum ether. The reaction product is then eluted with toluene, and is then recrystallized by extraction with pentane. Yield 400 mg (85%), m.p. 143°-143.5° C. Rf (silica gel/CHCl3)=0.94. UV (CHCl3): λmax (ε)=507 nm (31319), 482 (32213), 453 (sh, 17450). Fluorescence (CHCl3, exc. 507 nm) λmax (Irel)=539 (1), 557 (0.47).

Workup

  1. washthe purely aliphatic by-products are washed off with about 11 of petroleum ether
  2. washThe reaction product is then eluted with toluene
  3. customis then recrystallized by extraction with pentane

Sources & evidence

ORD record
ord-8d79b6fe34ed4df3b226e773c7c87732
Source dataset
uspto-grants-1997_07
Patent number
US05650513

Reaction notes

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