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

HRID 567355
Notes
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Reaction equation

HRID 567355 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent
2×

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-be730c92c0744fe99548a69368c35b5f
Source dataset
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06177440B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes