Water → HCID 15485782, compound

HRID 1356887Notes

Reaction equation

HRID 1356887 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=O)[CH2:11][C:12](=O)[CH:13]([F:15])[F:14])=[CH:9][C:4]=2[O:3][CH2:2]1.[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.O>C(O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:24]([C:23]4[CH:18]=[CH:19][C:20]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:21][CH:22]=4)[N:25]=[C:12]([CH:13]([F:15])[F:14])[CH:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 120809131-(1,3-Benzodioxol-5-yl)-4,4-difluoro-1,3-butanedione

Product 1

HCID 15485782HCID 15485782, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(1,3-Benzodioxol-5-yl)-4,4-difluorobutane-1,3-dione from Step 1 (2.4 g, 10 mmol) was dissolved in ethanol (100 mL). To the stirred mixture was added 4-sulfonamidophenylhydrazine hydrochloride (2.46 g, 11 mmol) and heated to reflux for 16 hours. The mixture was cooled and water was added until crystals slowly appeared. Filtration yielded a light tan solid (3.3 g, 84%): mp 214-218° C.; 1H NMR (D6-DMSO): 7.86 (d, J=8.7 Hz, 3H), 7.51 (d, J=8.7 Hz, 2H), 7.49 (brs, 2H), 7.3-6.7 (m, 5H, 6.06 s, 3H). Anal. Calc'd for C17H13N3SO4F2: C, 51.91; H, 3.33; N, 10.68. Found: C, 51.90; H, 3.25; N, 10.65.

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. temperatureThe mixture was cooled
  4. filtrationFiltration

Sources & evidence

ORD record
ord-ae8c0a69f9ac47049a2faf3d995dfea8
Source dataset
uspto-grants-2003_07
Patent number
US06586603B1

Reaction notes

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