Sebacoyl chloride → 1,10-Bis-[9-(4-acetyl-phenyl)-6-(thiophene-2-carbonyl)-carbazol-3-yl]-decane-1,10-dione

HRID 1801441

Reaction equation

HRID 1801441 reaction equation
[CH:1]1[C:13]2[N:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[C:28](Cl)=[O:29].[Al+3].[Cl-].[Cl-].[Cl-].[C:35](Cl)(=[O:47])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44](Cl)=[O:45]>C(Cl)Cl>[C:20]([C:17]1[CH:16]=[CH:15][C:14]([N:12]2[C:13]3[CH:1]=[CH:2][C:3]([C:35](=[O:47])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]([C:8]4[CH:9]=[CH:10][C:11]5[N:12]([C:14]6[CH:15]=[CH:16][C:17]([C:20](=[O:22])[CH3:21])=[CH:18][CH:19]=6)[C:13]6[C:5]([C:6]=5[CH:7]=4)=[CH:4][C:3]([C:28]([C:24]4[S:23][CH:27]=[CH:26][CH:25]=4)=[O:29])=[CH:2][CH:1]=6)=[O:45])=[CH:4][C:5]=3[C:6]3[C:11]2=[CH:10][CH:9]=[C:8]([C:28]([C:24]2[S:23][CH:27]=[CH:26][CH:25]=2)=[O:29])[CH:7]=3)=[CH:19][CH:18]=1)(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 66072Sebacoyl chlorideHCID 789282-Thiophenecarbonyl chlorideHCID 6451240Aluminum(III) Chloride2×HCID 99477551-[4-(9H-Carbazol-9-yl)phenyl]ethanone

Product 1

HCID 866405851,10-Bis-[9-(4-acetyl-phenyl)-6-(thiophene-2-carbonyl)-carbazol-3-yl]-decane-1,10-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-(4-carbazol-9-yl-phenyl)-ethanone (5.00 g) in CH2Cl2 (200 mL) is added thiophenecarbonyl chloride (2.56 g) and AlCl3 (4.74 g) at 0° C. After stirring overnight at room temperature, sebacoyl chloride (2.09 g) and AlCl3 (2.57 g) are further added at 0° C. and the mixture is stirred at room temperature overnight. The reaction mixture is poured into ice-water, and the crude product is extracted twice with CH2Cl2. The combined organic layer is washed with H2O and brine, dried over MgSO4, and concentrated to give the residue, which is purified by washing with hot ethyl acetate. The structure of the product, which is obtained as an orange solid, is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 1.38-1.51 (m, 8H), 1.82 (quint, 4H), 2.73 (s, 6H), 3.11 (t, 4H), 7.23 (t, 2H), 7.47 (d, 2H), 7.51 (d, 2H), 7.70-7.77 (m, 8H), 8.06 (d, 2H), 8.13 (d, 2H), 8.27 (d, 4H), 8.79 (s, 2H), 8.82 (s, 2H).

Workup

  1. stirringthe mixture is stirred at room temperature overnight
  2. extractionthe crude product is extracted twice with CH2Cl2
  3. washThe combined organic layer is washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give the residue, which
  7. customis purified
  8. washby washing with hot ethyl acetate
  9. customThe structure of the product, which is obtained as an orange solid

Sources & evidence

ORD record
ord-32c71263ff5146deb89baf1eac7ca62b
Source dataset
uspto-grants-2013_01
Patent number
US08349548B2

Linked notes

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