Hydrochloric Acid → 4-amino-N-(3-phenyl-1H-indazol-5-yl)benzenesulfonamide

HRID 25460Notes

Reaction equation

HRID 25460 reaction equation
Cl.[C:2]1([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][S:18]([C:21]4[CH:26]=[CH:25][C:24]([NH:27]C(=O)C)=[CH:23][CH:22]=4)(=[O:20])=[O:19])[CH:15]=3)[NH:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[NH4+]>C(O)C>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([S:18]([NH:17][C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[NH:10][N:9]=[C:8]3[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)(=[O:20])=[O:19])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14923Ammonium HydroxideHCID 22567164HCID 22567164, compound

Product 1

HCID 225673144-amino-N-(3-phenyl-1H-indazol-5-yl)benzenesulfonamideYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
20 °C

Procedure

4-Amino-N-(3-phenyl-1H-indazol-5-yl)benzenesulfonamide can be obtained in the following way: 1.5 ml of an aqueous 5N hydrochloric acid solution are added to a suspension of 0.3 g of N-[4-(3-phenyl-1H-indazol-5-ylsulfamoyl)-phenyl]acetamide in 6 ml of 95% ethanol. The reaction mixture is then refluxed for 30 minutes then cooled to a temperature in the region of 20° C. 20 ml of water and 1 ml of an aqueous 32% ammonium hydroxide solution are then added to the reaction mixture, which is then extracted successively with 30 ml and 15 ml of ethyl acetate. The organic extracts are pooled, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue thus obtained is purified by chromatography on a silica column (particle size 40-63 μm), eluting with a dichloromethane/methanol (95/5 by volume) mixture. The fractions containing the expected product are pooled and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The solid thus obtained is taken up in 9 ml of ethanol in the presence of 3S black and dissolved under hot conditions, and the mixture is filtered under hot conditions through sintered glass and then recrystallized. The crystals are filtered off through sintered glass, washed with 0.5 ml of 95% ethanol then with 2 times 2 ml of diisopropyl ether, partially dried and then dried under reduced pressure (3 kPa) at a temperature in the region of 50° C. 70 mg of 4-amino-N-(3-phenyl-1H-indazol-5-yl)benzenesulfonamide are thus obtained in the form of a light beige powder melting at 249° C. (CI mass analysis: m/z 365 (M+H)+).

Workup

  1. temperatureThe reaction mixture is then refluxed for 30 minutes
  2. extractionis then extracted successively with 30 ml and 15 ml of ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  6. customThe residue thus obtained
  7. customis purified by chromatography on a silica column (particle size 40-63 μm)
  8. washeluting with a dichloromethane/methanol (95/5 by volume) mixture
  9. additionThe fractions containing the expected product
  10. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  11. customThe solid thus obtained
  12. dissolutiondissolved under hot conditions
  13. filtrationthe mixture is filtered under hot conditions through sintered glass
  14. customrecrystallized
  15. filtrationThe crystals are filtered off through sintered glass
  16. washwashed with 0.5 ml of 95% ethanol
  17. dry with materialwith 2 times 2 ml of diisopropyl ether, partially dried
  18. customdried under reduced pressure (3 kPa) at a temperature in the region of 50° C

Sources & evidence

ORD record
ord-f5fb54a257e44d39b9c11087f44a544d
Source dataset
uspto-grants-2005_02
Patent number
US06858638B2

Reaction notes

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