Benzenesulfonamide → HCID 9954850, compound

HRID 1242123Notes

Reaction equation

HRID 1242123 reaction equation
[C:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([CH3:21])[N:10]2[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])=[CH:6][CH:5]=1)([OH:3])=O.[C:22]1([S:28]([NH2:31])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CN(C)C=O>[C:22]1([S:28]([NH:31][C:1]([C:4]2[CH:12]=[C:11]3[C:7]([CH:8]=[C:9]([CH3:21])[N:10]3[CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])=[CH:6][CH:5]=2)=[O:3])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7370BenzenesulfonamideHCID 9922346HCID 9922346, compoundHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 9954850HCID 9954850, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an N,N-dimethylformamide (10 ml) solution of 6-carboxy-1-(2-chlorobenzyl)-2-methylindole (0.470 g), added is N,N′-carbonyldiimidazole (0.508 g), and stirred at room temperature for 1 hour. Next, benzenesulfonamide (0.493 g) and diazabicycloundecene (0.477 g) are added thereto, and stirred at 100° C. for 72 hours. The solvent is evaporated away under reduced pressure, and the residue is purified through silica gel column chromatography (eluent: chloroform) to obtain 6-(benzenesulfonylcarbamoyl)-1-(2-chlorobenzyl)-2-methylindole. This is dissolved in a small amount of ethyl acetate, to which is added hexane. The crystal formed is taken out through filtration, and dried to obtain 6-(benzenesulfonylcarbamoyl)-1-(2-chlorobenzyl)-2-methylindole (32) (0.440 g).

Workup

  1. stirringstirred at 100° C. for 72 hours
  2. customThe solvent is evaporated away under reduced pressure
  3. customthe residue is purified through silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-8891e53248414523a2dbe42da96c0951
Source dataset
uspto-grants-2006_10
Patent number
US07115647B2

Reaction notes

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