Sulfanilamide → HCID 178464661, compound

HRID 1484464Notes

Reaction equation

HRID 1484464 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].[S:14]([NH2:24])(=[O:23])([C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1)=[O:15]>C(#N)C>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([S:14]([N:24]=[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:15])=[O:23])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 5333SulfanilamideHCID 67359253HCID 67359253, compound

Product 1

HCID 178464661HCID 178464661, compoundYield 86%

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 0.65 g (1.0 mol equiv.) sulfanilamide were added to 10 mL acetonitrile. The reaction mixture was refluxed overnight, and volatiles were removed underreduced 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:EtOAc=1:1) afforded 1.13 g (86%) 4-amino-N-[(4,4-dimethyl-4,5-dihydro-pyrazol-1-yl)-ethylamino-methylene]-benzenesulfonamide. 1H NMR (400 MHz, CDCl3) δ 1.15 (t, J=7.2 Hz, 3H), 1.20 (s, 6H), 3.43-3.51 (m, 2H), 3.74 (br.s., 2H), 3.98 (br.s., 2H), 6.66 (d, J=8.6 Hz, 2H), 6.71 (s, 1H), 7.71 (d, J=8.6 Hz, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customvolatiles were removed underreduced 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:EtOAc=1:1)

Sources & evidence

ORD record
ord-72865181de0c4c12a413f8efe73c5800
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

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