Benzyl Bromide → HCID 53764731, compound

HRID 1417463Notes

Reaction equation

HRID 1417463 reaction equation
[CH3:1][C:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[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:13]1[C:14]2[C:2]([CH3:1])=[C:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:4]=[CH:5][C:6]=2[C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=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 2549779H-Carbazole-2-carboxylic acid, 1-methyl-, ethyl ester

Product 1

HCID 53764731HCID 53764731, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 29 mg of ethyl 1-methylcarbazole-2-carboxylate in 1 ml of N,N-dimethylformamide was added, with ice-cooling, to a suspension of 10 mg of sodium hydride (55% w/w dispersion in mineral oil) in 2 ml of N,N-dimethylformamide. 29 mg of benzyl bromide was then added to the reaction mixture, which was then stirred for 1 hour, with ice-cooling. After this time, a saturated aqueous solution of ammonium chloride was added to the reaction mixture. The aqueous layer was extracted with ethyl acetate and the organic extract was washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography using 1 g of silica gel with a 9:1 v/v mixture of hexane and ethyl acetate as the eluent, to yield 38 mg of the title compound, melting at 79°-80° C.

Workup

  1. temperaturecooling
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. extractionthe organic extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. additionwith a 9:1 v/v mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-1882fce64b044a11b95fcbbf23349707
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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