Water → 9-hexylcarbazole

HRID 1633738Notes

Reaction equation

HRID 1633738 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].O>CN(C)C(=O)C>[CH2:17]([N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6854CarbazoleHCID 81011-BromohexaneHCID 24758Sodium hydride

Product 1

HCID 41256079-hexylcarbazole

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

20 g of carbazole was dissolved in 100 mL dry N,N-dimethyl acetamide (DMAc) in a 500 mL round bottomed flask. NaH (60% in mineral oil) was added into the flask slowly in nitrogen to form a mixture. The mixture was stirred for 20 minutes in ice/water bath. 30 g of 1-bromohexane was then added slowly to the flask and stirred for 6 hours in ice/water bath. The resulting solution was poured into 2L deionized water and extracted with ethyl acetate several times. The extract was re-extracted by deionized water. The final extract was concentrated by a rotary evaporator and further purified by column chromatography. A product of the following structure was obtained.

Workup

  1. customto form a mixture
  2. extractionextracted with ethyl acetate several times
  3. extractionThe extract was re-extracted by deionized water
  4. extractionThe final extract
  5. concentrationwas concentrated by a rotary evaporator
  6. customfurther purified by column chromatography
  7. customA product of the following structure was obtained

Sources & evidence

ORD record
ord-f2a4878f3b1f46d7a1d32af546fb39b7
Source dataset
uspto-grants-2003_01
Patent number
US06503998B2

Reaction notes

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