3-Chloro-4-methoxybenzenesulfonamide → HCID 178464673, compound

HRID 1484437Notes

Reaction equation

HRID 1484437 reaction equation
CS[C:3]([N:7]1[CH2:11][C:10]([CH3:13])([CH3:12])[CH:9]=[N:8]1)=[N:4][CH2:5][CH3:6].[Cl:14][C:15]1[CH:16]=[C:17]([S:23]([NH2:26])(=[O:25])=[O:24])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]>C(#N)C>[Cl:14][C:15]1[CH:16]=[C:17]([S:23]([N:26]=[C:3]([N:7]2[CH2:11][C:10]([CH3:12])([CH3:13])[CH:9]=[N:8]2)[NH:4][CH2:5][CH3:6])(=[O:24])=[O:25])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

4

Reactant 2

HCID 9670663-Chloro-4-methoxybenzenesulfonamideHCID 67359253HCID 67359253, compound

Product 1

HCID 178464673HCID 178464673, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.75 g (1 mol equiv.) N-Ethyl-4,4-dimethyl-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl ester and 0.94 g (1.05 mol equiv.) 3-chloro-4-methoxy-benzenesulfonamide were added to 10 mL acetonitrile. The reaction mixture was refluxed overnight and volatiles were removed in vacuo. 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 1.43 g (97%) 3-chloro-N-[(4,4-dimethyl-4,5-dihydro-pyrazol-1-yl)-ethylamino-methylene]-4-methoxy-benzenesulfonamide. 1H NMR (400 MHz, CDCl3) δ 1.17 (t, J=7.3 Hz, 3H), 1.22 (s, 6H), 3.43-3.52 (m, 2H), 3.77 (br.s., 2H), 3.95 (s, 3H), 6.75 (s, 1H), 6.96 (d, J=8.6 Hz, 1H), 6.70-6.90 (br.s., 1H) 7.82 (dd, J=8.6, 2.3 Hz, 1H), 7.95 (d, J=2.3 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customvolatiles were removed in vacuo
  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-1637e00ec13a46ac90cf43db5bd7c260
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

Loading…