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Water → 4-[5-(6-fluorobenzothiazol-2-yl)-3-trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonamide

HRID 369083
Notes
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Reaction equation

HRID 369083 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3](=O)[CH2:4][C:5]([C:7]1[S:8][C:9]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:10]=2[N:11]=1)=O.[S:20]([C:24]1[CH:29]=[CH:28][C:27]([NH:30][NH2:31])=[CH:26][CH:25]=1)(=[O:23])(=[O:22])[NH2:21].O>C(O)(=O)C>[F:16][C:14]1[CH:13]=[CH:12][C:10]2[N:11]=[C:7]([C:5]3[N:30]([C:27]4[CH:26]=[CH:25][C:24]([S:20]([NH2:21])(=[O:23])=[O:22])=[CH:29][CH:28]=4)[N:31]=[C:3]([C:2]([F:19])([F:18])[F:1])[CH:4]=3)[S:8][C:9]=2[CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 78105p-HydrazinobenzenesulphonamideHCID 232853611-(6-Fluorobenzothiazol-2-yl)-4,4,4-trifluorobutane-1,3-dione

Product 1

HCID 232854234-[5-(6-fluorobenzothiazol-2-yl)-3-trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonamideYield 42.7%

Reagents, catalysts & solvents 1

HCID 176Acetic Acid
Solvent

Procedure

The mixture of 4,4,4-trifluoro-1-(6-fluorobenzothiazol-2-yl)butane-1,3-dione (800 mg, 2.7 mmol) and 4-sulfamoylphenyl-hydrazine (720 mg, 3.8 mmol) was heated under reflux in acetic acid (10 ml) for 16 hours. After cooling, the reaction mixture was poured into water and extracted with methylene chloride. The organic layer was washed with water, dried over magnesium sulfate, and then evaporated. The residue was subjected to purification using chromatography on silica gel to afford 4-[5-(6-fluorobenzothiazol-2-yl)-3-trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonamide (510 mg, 42%) as a colorless needle. NMR(CDCl3 -DMSO-d6) δ: 6.70 (2H, bs), 7.22-7.39 (2H, m), 7.57-7.67 (3H, m), 7.91-7.96 (1H, m), 8.05 (2H, d, J=8.6 Hz); mp 260-261° C. (toluene)

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was subjected to purification

Sources & evidence

ORD record
ord-6ba7bc8e460b458dbeefa512c18032f3
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06136831

Reaction notes

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