4-Toluenesulfonyl chloride → Ethyl 5,8-dimethyl-9-p-toluenesulfonylcarbazole-4-carboxylate

HRID 1197171Notes

Reaction equation

HRID 1197171 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]2[C:5]=1[C:6]1[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:8][CH:9]=[CH:10][C:11]=1[NH:12]2.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>CN(C)C=O>[CH3:3][C:4]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]2[C:5]=1[C:6]1[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:8][CH:9]=[CH:10][C:11]=1[N:12]2[S:29]([C:26]1[CH:27]=[CH:28][C:23]([CH3:33])=[CH:24][CH:25]=1)(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 19897884Ethyl 5,8-dimethylcarbazole-4-carboxylate

Product 1

HCID 19897871Ethyl 5,8-dimethyl-9-p-toluenesulfonylcarbazole-4-carboxylateYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of 1.47 g of 60% sodium hydride (in a oil) in 35 ml of dry N,N-dimethylformamide was added dropwise over a 30 minutes period a solution of 7.00 g of ethyl 5,8-dimethylcarbazole-4-carboxylate obtained above in 35 ml of dry N,N-dimethylformamide, and the mixture was stirred for a further 30 minutes. To the mixture was added dropwise a solution of 6.99 g of p-toluenesulfonyl chloride in 35 ml of dry N,N-dimethyl-formamide, and the mixture was stirred further overnight. The reaction solution was poured into ice water and extracted with ethyl acetate, and the organic layer was washed, in turn, with dilute hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was chromatographed on silica gel column with hexane - ethyl acetate (9 : 1) to give 7.40 g of ethyl 5,8-dimethyl-9-p-toluenesulfonylcarbazole-4- carboxylate.

Workup

  1. stirringthe mixture was stirred further overnight
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed, in turn, with dilute hydrochloric acid
  4. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was chromatographed on silica gel column with hexane - ethyl acetate (9 : 1)

Sources & evidence

ORD record
ord-20bd1d5fe80b462ea253b9837e149a0f
Source dataset
uspto-grants-1992_05
Patent number
US05116995

Reaction notes

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