5-(9-acetyl-9H-carbazole-2-carbonyl)-2-chloro-benzenesulfonamide → HCID 66850484, compound

HRID 1515464Notes

Reaction equation

HRID 1515464 reaction equation
C([N:4]1[C:16]2[CH:15]=[C:14]([C:17]([C:19]3[CH:20]=[CH:21][C:22]([Cl:29])=[C:23]([S:25]([NH2:28])(=[O:27])=[O:26])[CH:24]=3)=[O:18])[CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=O)C>[OH-].[K+]>[CH:15]1[C:16]2[NH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:11]=2[CH:12]=[CH:13][C:14]=1[C:17]([C:19]1[CH:20]=[CH:21][C:22]([Cl:29])=[C:23]([S:25]([NH2:28])(=[O:26])=[O:27])[CH:24]=1)=[O:18]

Participants

3

Reactant 1

HCID 668506465-(9-acetyl-9H-carbazole-2-carbonyl)-2-chloro-benzenesulfonamide

Product 1

HCID 66850484HCID 66850484, compound

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A mixture of 0.5 g of 5-(9-acetyl-9H-carbazole-2-carbonyl)-2-chloro-benzenesulfonamide and 20 mL of potassium hydroxide solution (10% in water) is heated at reflux overnight and is allowed to cool to room temperature. The reaction mixture is extracted with ethyl acetate, washed with water then a saturated sodium chloride solution, and dried over sodium sulfate. After concentration the residue is loaded on Celite and purified by silica gel chromatography (1:1 hexanes/ethyl acetate) to give 5-(9H-carbazole-2-carbonyl)-2-chloro-benzenesulfonamide as dark orange crystals. MS (m/z): 385 (M+1).

Workup

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. extractionThe reaction mixture is extracted with ethyl acetate
  4. washwashed with water
  5. dry with materiala saturated sodium chloride solution, and dried over sodium sulfate
  6. concentrationAfter concentration the residue
  7. custompurified by silica gel chromatography (1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-14684b55fef7435691fe2b0225040a9a
Source dataset
uspto-grants-2012_07
Patent number
US08222424B2

Reaction notes

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