4-Hydrazinylbenzenesulfonamide hydrochloride → HCID 15293126, compound

HRID 1356900Notes

Reaction equation

HRID 1356900 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[CH2:14][CH2:13][C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:6]=2[N:24]([C:23]2[CH:18]=[CH:19][C:20]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:21][CH:22]=2)[N:25]=1

Participants

4

Reactant 2

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

Product 1

HCID 15293126HCID 15293126, compoundYield 71.2%

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 from Step 1 (1.21 g, 5.0 mmol), 4-sulfonamidophenylhydrazine hydrochloride (1.12 g, 5.0 mmol) and 25 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 concentrated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and isooctane to give 1.40 g, 71% of pure product: mp 257-258° C.; 1H NMR (CDCl3/CD3OD, 4:1) δ 2.7 (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); 19F NMR (CDCl3) δ −62.5. FAB-MS M+H=394.

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
  7. dry with materialwith brine, dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was recrystallized from a mixture of ethyl acetate and isooctane

Sources & evidence

ORD record
ord-fc08061db83d49b1971a42c4b63afbe8
Source dataset
uspto-grants-2003_07
Patent number
US06586603B1

Reaction notes

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