3-Chlorobenzenesulfonamide → HCID 178437239, compound

HRID 1484463Notes

Reaction equation

HRID 1484463 reaction equation
CS[C:3]([N:10]1[CH2:14][CH:13]([CH2:15][CH3:16])[CH:12]=[N:11]1)=[N:4][CH2:5][C:6]([F:9])([F:8])[F:7].[Cl:17][C:18]1[CH:19]=[C:20]([S:24]([NH2:27])(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1>C(#N)C>[Cl:17][C:18]1[CH:19]=[C:20]([S:24]([N:27]=[C:3]([N:10]2[CH2:14][CH:13]([CH2:15][CH3:16])[CH:12]=[N:11]2)[NH:4][CH2:5][C:6]([F:7])([F:8])[F:9])(=[O:25])=[O:26])[CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 5193773-ChlorobenzenesulfonamideHCID 673591964-ethyl-N-(2,2,2-trifluoro-ethyl)-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl ester

Product 1

HCID 178437239HCID 178437239, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.57 g (1 mol equiv.) 4-Ethyl-N-(2,2,2-trifluoro-ethyl)-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl ester and 3.0 g (6.8 mol equiv.) 3-chloro-benzenesulfonamide were added to 20 mL acetonitrile. The reaction mixture was refluxed for 72 hours, and volatiles were removed under reduced pressure. The residue was taken up in ethyl acetate and extracted with 2N NaOH. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. Purification by flash chromatography on silica gel (Et2O:PA=1:1) afforded 0.36 g (38%) 3-chloro-N-[(4-ethyl-4,5-dihydro-pyrazol-1-yl)-(2,2,2-trifluoro-ethylamino)-methylene]-benzenesulfonamide. 1H NMR (400 MHz, CDCl3) δ 1.00 (t, J=7.5 Hz, 3H), 1.51-1.74 (m, 2H), 3.16-3.27 (m, 1H), 3.87 (dd, J=11.2, 7.5 Hz, 1H), 4.03-4.14 (m, 2H), 4.28 (t, J=11.2 Hz, 1H), 7.03 (d, J=1.5 Hz, 1H), 7.41 (t, J=7.8 Hz, 1H), 7.46-7.50 (m, 1H), 7.79-7.84 (m, 1H), 7.91-7.94 (m, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 72 hours
  2. customvolatiles were removed under reduced pressure
  3. extractionextracted with 2N NaOH
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customPurification by flash chromatography on silica gel (Et2O:PA=1:1)

Sources & evidence

ORD record
ord-f6094356e3ee48ce8fede06a4eb6027b
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

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