Pyridine → 3-nitro-N-(3-phenyl-1H-indazol-5-yl)benzenesulfonamide

HRID 25461

Reaction equation

HRID 25461 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][N:19]=[C:18]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.N1C=CC=CC=1>C1COCC1.O.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([NH:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[C:18]3[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 3

HCID 1049PyridineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 224801043-Phenyl-1H-indazol-5-amine

Product 1

HCID 225673203-nitro-N-(3-phenyl-1H-indazol-5-yl)benzenesulfonamideYield 31.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

3-Nitro-N-(3-phenyl-1H-indazol-5-yl)benzenesulfonamide can be obtained in the following way: 0.89 g of 3-nitrobenzenesulfonyl chloride is added to a solution, at a temperature in the region of 0° C. and under argon, of 0.7 g of 5-amino-3-phenyl-1H-indazole in 15 ml of THF. The reaction mixture is cooled to a temperature in the region of 0° C., and then a solution of 0.33 ml of pyridine in 4 ml of THF is added over 10 minutes. The reaction mixture is stirred at a temperature in the region of 0° C. for 0.5 hours then at a temperature in the region of 20° C. for 3 hours. It is then diluted with 70 ml of water and 30 ml of ethyl acetate. After settling out, the organic phase is washed with 3 times 50 ml of water, 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 63-200 μm), eluting with pure dichloromethane then with a dichloromethane/methanol (98/2 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 residue is taken up in 20 ml isopropanol and filtered through sintered glass. The solid is washed with 10 ml of diisopropyl ether, partially dried and then dried. 0.41 g of 3-nitro-N-(3-phenyl-1H-indazol-5-yl)benzenesulfonamide is thus obtained in the form of a white powder melting at 228° C. (analysis: C19H14N4O4S (0.44 CH2Cl2): % calculated C, 57.85; H, 3.58; N, 14.21; O, 16.23; S, 8.13. % found C, 57.84; H, 3.19; N, 14.22; S, 7.81).

Workup

  1. waitat a temperature in the region of 20° C. for 3 hours
  2. washthe organic phase is washed with 3 times 50 ml of water
  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 63-200 μm)
  8. washeluting with pure dichloromethane
  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. filtrationfiltered through sintered glass
  12. washThe solid is washed with 10 ml of diisopropyl ether
  13. custompartially dried
  14. customdried

Sources & evidence

ORD record
ord-f563b60430824a3f93e1223c3a2ea404
Source dataset
uspto-grants-2005_02
Patent number
US06858638B2

Linked notes

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