2-Thiophenecarbonyl chloride → (E)-1-[9-(4-Acetyl-phenyl)-6-(thiophene-2-carbonyl)-carbazol-3-yl]-but-2-en-1-one

HRID 1402647Notes

Reaction equation

HRID 1402647 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:39])/[CH:36]=[CH:37]/[CH3:38]>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:39])/[CH:36]=[CH:37]/[CH3:38])=[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 789282-Thiophenecarbonyl chlorideHCID 643131trans-Crotonyl chlorideHCID 6451240Aluminum(III) Chloride2×HCID 99477551-[4-(9H-Carbazol-9-yl)phenyl]ethanone

Product 1

HCID 68599881(E)-1-[9-(4-Acetyl-phenyl)-6-(thiophene-2-carbonyl)-carbazol-3-yl]-but-2-en-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-(4-carbazol-9-yl-phenyl)ethanone (30.0 g) in CH2Cl2 (1200 mL) is added thiophenecarbonyl chloride (15.4 g) and AlCl3 (28.4 g) at 0° C. After stirring overnight at room temperature, crotonyl chloride (11.3 g) and AlCl3 (15.5 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.

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

Sources & evidence

ORD record
ord-238082f183634eee9043131d883c4d91
Source dataset
uspto-grants-2014_12
Patent number
US08911921B2

Reaction notes

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