Imidazole → HCID 19033220, 화합물

HRID 266609

반응식

HRID 266609 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].[C:26]([C:30]1[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[C:34]([C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:33][C:31]=1[NH2:32])([CH3:29])([CH3:28])[CH3:27].N1C=CN=C1>O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[C:26]([C:30]1[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[C:34]([C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:33][C:31]=1[N:32]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])([CH3:29])([CH3:28])[CH3:27]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 81670782,5-Ditert-butyl-4-nitroanilineHCID 11759069Perylene-3,4-dicarboxylic anhydride

생성물 1

HCID 19033220HCID 19033220, 화합물

시약·촉매·용매 1

HCID 2724192Zinc acetate (USP)촉매

반응 조건

온도
170 °C

실험 절차

0.20 g (0.93 mmol) of perylene-3,4-dicarboxylic anhydride is mixed with 0.47 g (1.9 mmol) of 2,5-di-t-butyl-4-nitroaniline, 0.20 g of zinc acetate dihydrate and 4 g of imidazole, and the mixture is heated under argon at 170° C. for 22 h. The product is removed from the flask by washing with ethanol, treated with 2N hydrochloric acid and then boiled until all the ethanol has evaporated. The solid product is filtered off with suction, washed twice with water and then boiled in 10% potassium carbonate solution. The reaction product is again filtered off with suction while hot and washed several times with hot water until the filtrate run-off is no longer yellow. The residue is dried in a drying cabinet at 120° C. and then chromatographed on silica gel using toluene. The solution thus obtained is filtered through a D5 sintered crucible in order to remove any adhering silica gel. Yield 0.09 g (26%) of a red powder showing a red solid fluorescence, m.p. >360° C., Rf (CHCl3 /silica gel)=0.31, UV (CHCl3): λmax (ε)=514 (24450), 489 (25850), 356 (3100), 265 (33790). Fluorescence (CHCl3): λmax (Ired)=543 (1), 576 (0.45).

후처리

  1. customThe product is removed from the flask
  2. washby washing with ethanol
  3. additiontreated with 2N hydrochloric acid
  4. customhas evaporated
  5. filtrationThe solid product is filtered off with suction
  6. washwashed twice with water
  7. filtrationThe reaction product is again filtered off with suction while hot and
  8. washwashed several times with hot water until the filtrate
  9. customThe residue is dried in a drying cabinet at 120° C.
  10. customchromatographed on silica gel
  11. customThe solution thus obtained
  12. filtrationis filtered through a D5 sintered crucible in order
  13. customto remove any adhering silica gel

출처 및 근거

ORD 기록
ord-7e5c08cb5ae045478ee1ab69a3852ef0
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05650513

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