Carbazole → HCID 15110912, compound

HRID 1914260Notes

Reaction equation

HRID 1914260 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+].[I:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]I>C1COCC1>[I:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][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

Participants

5

Reactant 3

HCID 6854CarbazoleHCID 123731,6-DiiodohexaneHCID 24758Sodium hydride

Product 1

HCID 15110912HCID 15110912, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of carbazole (0.5 g, 2.99 mmoles) in THF (6 mL), NaH (0.25 g, 6 mmoles) was slowly added. The mixture was stirred for 1 hour giving a solution. The resulting solution was introduced under nitrogen in a dropping funnel and slowly added in 10 minutes to a solution of 1,6-diiodo hexane (3 ml, 18 mmoles) in THF (2 mL). The reaction mixture stirred for 2 hours at room temperature, it was quenched with water and ice and THF was evaporated under reduced pressure. The mixture was extracted with ethyl ether (3×5 mL) and the organic phases were collected and combined, dried over Na2SO4 and evaporated under reduced pressure. The crude product was purified by chromatography (from n-hexane to n-hexane:CH2Cl2 10:1). Yield: 83%. Rf=0.55 (cyclohexane/dichloromethane 3/1).

Workup

  1. additionwas slowly added
  2. customgiving a solution
  3. additionThe resulting solution was introduced under nitrogen in a dropping funnel
  4. stirringThe reaction mixture stirred for 2 hours at room temperature
  5. customit was quenched with water and ice and THF
  6. customwas evaporated under reduced pressure
  7. extractionThe mixture was extracted with ethyl ether (3×5 mL)
  8. customthe organic phases were collected
  9. dry with materialdried over Na2SO4
  10. customevaporated under reduced pressure
  11. customThe crude product was purified by chromatography (from n-hexane to n-hexane:CH2Cl2 10:1)

Sources & evidence

ORD record
ord-ba16752a8db04514abc7e3dd7b08d759
Source dataset
uspto-grants-2013_12
Patent number
US08610111B2

Reaction notes

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