Benzyl Bromide → 9-Benzyl-5-carbamoyl-4-methoxy-1-methylcarbazole

HRID 51442Notes

Reaction equation

HRID 51442 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:5]=1[C:6]1[C:7]([O:18][CH3:19])=[CH:8][CH:9]=[C:10]([CH3:17])[C:11]=1[NH:12]2)(=[O:3])[NH2:2].[H-].[Na+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Cl-].[NH4+]>CN(C)C=O>[CH2:22]([N:12]1[C:11]2[C:10]([CH3:17])=[CH:9][CH:8]=[C:7]([O:18][CH3:19])[C:6]=2[C:5]2[C:13]1=[CH:14][CH:15]=[CH:16][C:4]=2[C:1](=[O:3])[NH2:2])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22738585HCID 22738585, compound

Product 1

HCID 227394469-Benzyl-5-carbamoyl-4-methoxy-1-methylcarbazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 0.148 g of 5-carbamoyl-4-methoxy-1-methylcarbazole in 1.1 ml of dimethylformamide was added to 0.026 g of sodium hydride (60% in mineral oil) in 0.4 ml of dimethylformamide and stirred for 60 minutes at room temperature. Benzyl bromide (0.076 ml) was then added and the reaction was stirred overnight. The reaction mixture was poured into 20 ml of saturated ammonium chloride solution and then extracted twice with ethyl acetate. The extracts were washed with water and then with brine, dried over magnesium sulfate and concentrated. The residue was rinsed with hexane and dissolved in dichloromethane, filtered and concentrated to afford 0.21 g of the subtitle compound. FDMS m/e 344 (M+).

Workup

  1. stirringthe reaction was stirred overnight
  2. extractionextracted twice with ethyl acetate
  3. washThe extracts were washed with water
  4. dry with materialwith brine, dried over magnesium sulfate
  5. concentrationconcentrated
  6. washThe residue was rinsed with hexane
  7. dissolutiondissolved in dichloromethane
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-7cb721b04f754d64bf168ae69008dd51
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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