Sodium hydride → HCID 66980816, compound

HRID 2172369Notes

Reaction equation

HRID 2172369 reaction equation
[CH:1]1[C:17]2[C:16]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[NH:9][C:8]=3[CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:21][CH:22]([CH2:27][CH3:28])[CH2:23][CH2:24][CH2:25][CH3:26]>CN(C)C=O>[CH2:27]([CH:22]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:21][N:9]1[C:8]2[CH:7]=[CH:6][C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:17]=3[C:16]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2)[CH3:28]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 674597H-Benzo(c)carbazoleHCID 868042-Ethylhexyl bromide

Product 1

HCID 66980816HCID 66980816, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 7H-benzo[c]carbazole (0.78 g, 3.59 mmol) in dimethylformamide (DMF) (4 ml) is added sodium hydride (0.21 g, 5.21 mmol) at 0° C., and the mixture is stirred for 1 hour. To the reaction mixture is added 1-bromo-2-ethylhexane (1.04 g, 5.39 mmol). The mixture is stirred at room temperature overnight, and then at 0° C. for 5 hours. After the reaction mixture is cooled at room temperature, it is poured into ice-water, and the crude product is extracted with AcOEt, and washed with water and brine. After drying over MgSO4 and concentration, the desired product is obtained as a brown liquid (1.21 g, 99%). The structure is confirmed by 1H-NMR spectrum (CDCl3) δ [ppm]: 0.83-0.92 (m), 1.20-1.43 (m), 2.07-2.10 (m), 4.24-4.38 (m), 7.37 (td), 7.44-7.50 (m), 7.52-7.54 (m), 7.62 (d), 7.69 (td), 7.87 (d), 7.99 (d), 8.59 (d), 8.80 (d)

Workup

  1. stirringThe mixture is stirred at room temperature overnight
  2. waitat 0° C. for 5 hours
  3. extractionthe crude product is extracted with AcOEt
  4. washwashed with water and brine
  5. dry with materialAfter drying over MgSO4 and concentration

Sources & evidence

ORD record
ord-90d97ad4dd424c13b36995319df36383
Source dataset
uspto-grants-2015_06
Patent number
US09051397B2

Reaction notes

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