1-Butanesulfonamide → HCID 21938319, compound

HRID 1242146Notes

Reaction equation

HRID 1242146 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH3:13])=[C:7]2[C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])(O)=[O:2].[CH2:24]([S:28]([NH2:31])(=[O:30])=[O:29])[CH2:25][CH2:26][CH3:27].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CN(C)C=O>[CH2:24]([S:28]([NH:31][C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH3:13])=[C:7]2[C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])=[O:2])(=[O:30])=[O:29])[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 184601-ButanesulfonamideHCID 21938222HCID 21938222, compoundHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 21938319HCID 21938319, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to the method of Example 59, 5-carboxy-3-(2,4-dichlorobenzoyl)-2-methylindole (0.500 g) is suspended in N,N-dimethylformamide (10 ml), to which is added N,N′-carbonyldiimidazole (0.350 g), and stirred at room temperature for 2 hours. Next, 1-butanesulfonamide (0.296 g) and diazabicycloundecene (0.328 g) are added thereto, and stirred under heat at 100° C. for 6 hours. The reaction mixture is concentrated under reduced pressure, and the residue is made acidic with water and 3 M HCl added thereto, and then extracted with ethyl acetate. The organic layer is washed with a saturated saline solution, and dried with anhydrous sodium sulfate. The drying agent is removed through filtration, and the filtrate is concentrated under reduced pressure. The resulting oily residue is purified through silica gel column chromatography (eluent: chloroform methanol=10/), and recrystallized from ethanol-hexane to obtain a colorless crystal of 5-(1-butanesulfonylcarbamoyl)-3-(2,4-dichlorobenzoyl)-2-methylindole (97) (0.420 g).

Workup

  1. stirringstirred
  2. temperatureunder heat at 100° C. for 6 hours
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. additionadded
  5. extractionextracted with ethyl acetate
  6. washThe organic layer is washed with a saturated saline solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. customThe drying agent is removed through filtration
  9. concentrationthe filtrate is concentrated under reduced pressure
  10. customThe resulting oily residue is purified through silica gel column chromatography (eluent: chloroform methanol=10/)
  11. customrecrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-efbfb3d91ffa4548aadf43538de1410a
Source dataset
uspto-grants-2006_10
Patent number
US07115647B2

Reaction notes

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