Aluminum(III) Chloride → HCID 19808830, compound

HRID 374021Notes

Reaction equation

HRID 374021 reaction equation
[C:1]1([N:7]2[C:23](=[O:24])[C:22]3[C:21]4[C:20]5[C:15](=[CH:16][C:17]([Br:27])=[C:18]([O:25][CH3:26])[CH:19]=5)[N:14](CC5C=CC=CC=5)[C:13]=4[C:12]([CH2:35][N:36]([CH3:38])[CH3:37])=[CH:11][C:10]=3[C:8]2=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C1(OC)C=CC=CC=1>[C:1]1([N:7]2[C:23](=[O:24])[C:22]3[C:21]4[C:20]5[C:15](=[CH:16][C:17]([Br:27])=[C:18]([O:25][CH3:26])[CH:19]=5)[NH:14][C:13]=4[C:12]([CH2:35][N:36]([CH3:37])[CH3:38])=[CH:11][C:10]=3[C:8]2=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 19808762HCID 19808762, compound

Product 1

HCID 19808830HCID 19808830, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

350 mg of N-phenyl-9-benzyl-7-bromo-1-dimethylaminomethyl-6-methoxycarbazole-3,4-dicarboximide was suspended in 5 ml of anisole. To the suspension was added 410 mg of anhydrous aluminum chloride. The resulting mixture was stirred for 120 hours at room temperature. The solvent was removed by distillation under reduced pressure. To the residue was added 20 ml of an aqueous saturated sodium hydrogencarbonate solution. The resulting mixture was stirred for 10 minutes at room temperature. The insoluble material was collected by filtration and was subjected to extraction with four 50-ml portions of chloroform. The extract was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: chloroform) to obtain 250 mg (yield: 85%) of N-phenyl-7-bromo-1-dimethylaminomethyl-6-methoxycarbazole-3,4-dicarboximide as yellow amorphous product.

Workup

  1. customThe solvent was removed by distillation under reduced pressure
  2. additionTo the residue was added 20 ml of an aqueous saturated sodium hydrogencarbonate solution
  3. stirringThe resulting mixture was stirred for 10 minutes at room temperature
  4. filtrationThe insoluble material was collected by filtration
  5. extractionwas subjected to extraction with four 50-ml portions of chloroform
  6. washThe extract was washed with an aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed by distillation under reduced pressure
  9. customThe residue was purified by column chromatography (eluant: chloroform)

Sources & evidence

ORD record
ord-1e5726d7a9064d2789f639d3228a66a3
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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