Water → N-[3-(4-chlorophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide

HRID 1452864

Reaction equation

HRID 1452864 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11](Cl)(=[O:13])=[O:12])(=[O:4])=[O:3].[NH2:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][N:20]=[C:19]2[C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1.N1C=CC=CC=1.O>O1CCCC1>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([C:19]2[C:18]3[C:22](=[CH:23][CH:24]=[C:16]([NH:15][S:11]([C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=4[S:2]([CH3:1])(=[O:4])=[O:3])(=[O:13])=[O:12])[CH:17]=3)[NH:21][N:20]=2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 27351782-Methanesulfonylbenzene-1-sulfonyl chlorideHCID 225671693-(4-chlorophenyl)-1H-indazol-5-amine

Product 1

HCID 22567333N-[3-(4-chlorophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamideYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-[3-(4-Chlorophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide can be obtained in the following way: a solution of 0.515 g 2-methylsulfonylbenzenesulfonyl chloride in 3 ml of tetrahydrofuran is added dropwise to a solution, cooled to 0° C., of 0.45 g of 5-amino-3-(4-chlorophenyl)-1H-indazole, of 15 ml of tetrahydrofuran and of 0.165 ml of pyridine. After reacting for 30 minutes at a temperature in the region of 0° C. and 2 hours at a temperature in the region of 20° C., 50 ml of distilled water are added to the reaction medium. The medium is extracted with 30 ml of ethyl acetate. The organic phase is then washed with 3 times 20 ml of distilled water and the aqueous phase is extracted again with 30 ml of ethyl acetate. The organic phases are pooled, dried over magnesium sulfate, filtered and concentrated to dryness by evaporation under reduced pressure. The residue thus obtained is purified by chromatography on a silica column with a dichloromethane/ethyl acetate (99/1 by volume) mixture as eluent. 0.79 g of N-[3-(4-chlorophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide is thus obtained in the form of a white powder melting at 242° C. (analysis C20H16ClN3O4S2.0.65CH3OH % calculated C, 52.01; H, 3.49; Cl, 7.67; N, 9.10; O, 13.85; S, 13.88. % found C, 52.02; H, 3.78; Cl, 7.91; N, 9.21; S, 13.45).

Workup

  1. additionare added to the reaction medium
  2. extractionThe medium is extracted with 30 ml of ethyl acetate
  3. washThe organic phase is then washed with 3 times 20 ml of distilled water
  4. extractionthe aqueous phase is extracted again with 30 ml of ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness by evaporation under reduced pressure
  8. customThe residue thus obtained
  9. customis purified by chromatography on a silica column with a dichloromethane/ethyl acetate (99/1 by volume) mixture as eluent

Sources & evidence

ORD record
ord-2680b8b488c24f189609a4d9b56112f9
Source dataset
uspto-grants-2009_01
Patent number
US07473701B2

Linked notes

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