3-Chlorobenzenesulfonamide → HCID 178464647, compound

HRID 1484447Notes

Reaction equation

HRID 1484447 reaction equation
CS[C:3]([N:7]1[CH:11]([C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH2:10][CH:9]=[N:8]1)=[N:4][CH2:5][CH3:6].[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]([NH:4][CH2:5][CH3:6])[N:7]2[CH:11]([C:12]3[CH:16]=[CH:15][S:14][CH:13]=3)[CH2:10][CH:9]=[N:8]2)(=[O:25])=[O:26])[CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 5193773-ChlorobenzenesulfonamideHCID 67360167HCID 67360167, compound

Product 1

HCID 178464647HCID 178464647, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.47 g (1 mol equiv.) N-Ethyl-5-thiophen-3-yl-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl ester and 0.37 g (1.05 mol equiv.) 3-chlorobenzenesulfonamide were added to 7 mL acetonitrile. The reaction mixture was refluxed overnight 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) afforded 0.44 g (49%) 3-chloro-N-[ethylamino-(5-thiophen-3-yl-4,5-dihydro-pyrazol-1-yl)-methylene]-benzenesulfonamide. 1H NMR (400 MHz, CDCl3) δ 1.19 (t, J=7.2, 3H), 2.78 (ddd, J=18.6, 6.0, 1.4 Hz, 1H), 3.31 (ddd, J=18.6, 11.8, 1.4 Hz, 1H), 3.54-3.70 (m, 2H), 5.62 (dd, J=11.8, 6.0 Hz, 1H), 6.75 (d, J=4.3 Hz, 1H), 6.92 (d, J=2.0 Hz, 1H), 7.02 (br.s., 1H), 7.17-7.23 (m, 2H), 7.36 (m, 2H), 7.54 (br.s., 1H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  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)

Sources & evidence

ORD record
ord-c8d86c580c134128a2b4615cd330b4cc
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

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