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

HRID 266600
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HRID 266600 반응식
[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]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].N1C=CN=C1.Cl>O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C.C(O)C>[CH2:28]([CH:27]([N:26]1[C:21](=[O:22])[C:5]2[C:4]3[C:19]4[C:8](=[CH:7][CH:6]=2)[C:9]2[C:20]5[C:13]([CH:12]=[CH:11][CH:10]=2)=[CH:14][CH:15]=[CH:16][C:17]=5[C:18]=4[CH:1]=[CH:2][C:3]=3[C:24]1=[O:23])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 574991Tridecan-7-amineHCID 11759069Perylene-3,4-dicarboxylic anhydride

생성물 1

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

시약·촉매·용매 2

HCID 2724192Zinc acetate (USP)촉매
HCID 702Ethanol용매2회

실험 절차

200 mg (620 mmol) of perylene-3,4-dicarboxylic anhydride (prepared according to Example 20, below) are heated together with 250 mg (0.12 mmol) of 7-aminotridecane, 110 mg of zinc acetate dihydrate and 1.2 g of imidazole under an argon inert atmosphere at 135°-140° C. for 1 h. After cooling, the dark-red melt cake is digested with 100 ml of ethanol, and 100 ml of 15 per cent hydrochloric acid are added to the resulting suspension, and the mixture is boiled until all the ethanol has evaporated (the reaction product is readily soluble in ethanol). The solid is filtered off with suction and washed with warm water until the filtrate run-off no longer gives a yellow fluorescence. The crude product is then dried in a drying cabinet at 120° C. for 2 h and then chromatographed on silica gel using chloroform. The first coloured fraction is recrystallized by extraction with methanol. Yield 200 mg (63%) orange-red crystals showing strong solid fluorescence, m.p. 166°-168° C. Rf (chloroform/silica gel)=0.87. UV (CHCl3): λmax (ε)=506 (30250), 484 (31580). Fluorescence (CHCl3, exc. 506 nm) λmax (Irel): 540 (1), 568 (0.52).

후처리

  1. temperatureAfter cooling
  2. additionare added to the resulting suspension
  3. customhas evaporated (the reaction product
  4. filtrationThe solid is filtered off with suction
  5. washwashed with warm water until the filtrate run-off
  6. customno longer gives a yellow fluorescence
  7. dry with materialThe crude product is then dried in a drying cabinet at 120° C. for 2 h
  8. customchromatographed on silica gel
  9. customThe first coloured fraction is recrystallized by extraction with methanol

출처 및 근거

ORD 기록
ord-381e5b74a4f64139b820839bedd21f4a
출처 데이터셋
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05650513

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