4-Hydrazinylbenzenesulfonamide hydrochloride → HCID 22315385, compound

HRID 1939302Notes

Reaction equation

HRID 1939302 reaction equation
[F:1][CH:2]([F:18])[C:3](=[C:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[C:6]1=O)O.[CH:19]1[C:24]([NH:25][NH2:26])=[CH:23][CH:22]=[C:21]([S:27]([NH2:30])(=[O:29])=[O:28])[CH:20]=1.Cl>C(O)C>[F:1][CH:2]([F:18])[C:3]1[C:5]2[CH2:14][CH2:13][C:12]3[CH:11]=[C:10]([O:15][CH3:16])[CH:9]=[CH:8][C:7]=3[C:6]=2[N:25]([C:24]2[CH:19]=[CH:20][C:21]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:22][CH:23]=2)[N:26]=1

Participants

4

Reactant 2

HCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 178487169HCID 178487169, compound

Product 1

HCID 22315385HCID 22315385, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 500 mL one neck round bottomed flask equipped with reflux condenser, nitrogen inlet and provisions for magnetic stirring was charged with 3,4-dihydro-6-methoxy-2-[2,2-difluoro-1-hydroxyethylidene]-1(2H)-naphthalenone from Step 1 (2.54 g, 10 mmol), 4-sulfonamidophenylhydrazine hydrochloride (2.91 g, 13 mmol) and 250 mL of absolute ethanol. The solution was warmed to reflux for 15 hours and concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with water and with brine, dried over anhydrous MgSO4, filtered and reconcentrated in vacuo. The residue was recrystallized from a mixture of ethanol and water to give 4-[3-(difluoromethyl)-4,5-dihydro-7-methoxy-1H-benz[g]indazol-1-yl]benzenesulfonamide (3.3 g, 82%): mp 256°-257° C.

Workup

  1. temperaturewith reflux condenser, nitrogen inlet
  2. temperatureThe solution was warmed
  3. temperatureto reflux for 15 hours
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with water and with brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. customThe residue was recrystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-409d167f23cc442c9f9cd530a8a63e45
Source dataset
uspto-grants-1997_12
Patent number
US05696143

Reaction notes

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