Water → HCID 12080915, compound

HRID 1292309Notes

Reaction equation

HRID 1292309 reaction equation
[Cl:1][CH:2]([Cl:17])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([F:15])[CH:8]=1)=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.O>C(O)C>[Cl:1][CH:2]([Cl:17])[C:3]1[CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([F:15])[CH:8]=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

5

Reactant 3

HCID 962WaterHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 22315573HCID 22315573, compound

Product 1

HCID 12080915HCID 12080915, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4,4-Dichloro-1-(3-fluoro-4-methoxyphenyl)-butane-1,3-dione from Step 2 (2.8 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 (2.7 g, 63 %) : mp 190°-193° C.; 1H NMR (DMSO-d6) 7.84 (d, J=8.4 Hz, 2H), 7.53 (s, 1H), 7.48 (d, J=8.4 Hz, 2H), 7.47 (brs, 2H), 7.3-7.0 (m, 3H), 6.95 (s, 1H), 3.85 (s, 3H). Anal. Calc'd for C17 H14N3SO3FCl2 : C, 47.45; H, 3.28; N, 9.76. Found: C, 47.68; H, 3.42; N, 10.04.

Workup

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

Sources & evidence

ORD record
ord-f9dd93ce31354e008b83ee1f89b7f430
Source dataset
uspto-grants-1998_05
Patent number
US05756529

Reaction notes

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