4-Hydrazinylbenzenesulfonamide hydrochloride → 4,5-dihydro-4-[3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamide

HRID 129213

Reaction equation

HRID 129213 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=O)=O.[CH:18]1[C:23]([NH:24][NH2:25])=[CH:22][CH:21]=[C:20]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:19]=1.Cl>C(O)C>[F:1][C:2]([F:17])([F:16])[C:3]1[C:5]2[C:6](=[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]3=[CH:13][CH:14]=2)[N:24]([CH:23]2[CH2:22][CH:21]=[C:20]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:19]=[CH:18]2)[N:25]=1

Participants

4

Reactant 2

HCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 69171222-Trifluoroacetyl-1-tetralone

Product 1

HCID 189203554,5-dihydro-4-[3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamideYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 100 mL one necked round bottomed flask equipped with reflux condenser nitrogen inlet and provisions for magnetic stirring was charged with 2-trifluoroacetyl-1-tetralone (1.21 g, 5.0 mmol), 4-sulfonamido phenylhydrazine hydrochloride (1.12 g, 5.0 mmol) and 25 mL of absolute ethanol. The solution was then warmed to reflux for 15 h and then concentrated in vacuo. The residue was dissolved in ethyl acetate and then washed with water, brine, dried over anhyd. MgSO4, filtered and concentrated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and isooctane to give g, 71% of pure product with mp 257°-258° C. 1H NMR (CDCl3 /CD3OD, 4:1) δ2.7 (m, 2H), 2.9 (m, 2H), 6.6 (m, 1H), 6.9 (m, 1H), 7.1 (m, 1H), 7.16 (m, 1H), 7.53 (m, 2H), 7.92 (m, 2H); 19 F NMR CDCl3 δ62.5. FAB-MS M+H=394.

Workup

  1. temperaturewith reflux condenser nitrogen inlet
  2. temperatureThe solution was then warmed
  3. temperatureto reflux for 15 h
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with water, brine
  7. customdried over anhyd
  8. filtrationMgSO4, filtered
  9. concentrationconcentrated in vacuo
  10. customThe residue was recrystallized from a mixture of ethyl acetate and isooctane

Sources & evidence

ORD record
ord-87f60829f74e4792a3a28adfd4d77a79
Source dataset
uspto-grants-1995_11
Patent number
US05466823

Linked notes

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