5-Chlorothiophene-2-Sulfonamide → 5-Chloro-thiophene-2-sulfonic acid amino-(4,4-dimethyl-4,5-dihydro-pyrazol-1-yl)-methyleneamide

HRID 1484460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1484460
CS[C:3]([N:5]1[CH2:9][C:8]([CH3:11])([CH3:10])[CH:7]=[N:6]1)=[NH:4].[Cl:12][C:13]1[S:17][C:16]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:15][CH:14]=1>C(#N)C>[NH2:4][C:3]([N:5]1[CH2:9][C:8]([CH3:11])([CH3:10])[CH:7]=[N:6]1)=[N:21][S:18]([C:16]1[S:17][C:13]([Cl:12])=[CH:14][CH:15]=1)(=[O:20])=[O:19]

Komponenten

4

Edukt 2

HCID 12413015-Chlorothiophene-2-SulfonamideHCID 673594724,4-Dimethyl-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl ester

Produkt 1

HCID 699280035-Chloro-thiophene-2-sulfonic acid amino-(4,4-dimethyl-4,5-dihydro-pyrazol-1-yl)-methyleneamideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1.0 g (1 mol equiv.) 4,4-Dimethyl-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl ester and 1.21 g (1.05 mol equiv.) 5-chloro-thiophene-2-sulfonic acid amide were added to 10 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:PA=2:1) afforded 1.58 g (80%) 5-chloro-thiophene-2-sulfonic acid amino-(4,4-dimethyl-4,5-dihydro-pyrazol-1-yl)-methyleneamide. 1H NMR (400 MHz, CDCl3) δ 1.25 (s, 6H), 3.63 (s, 2H), 6.00-6.50 (br.s., 1H), 6.79 (s, 1H), 6.85 (d, J=4.0 Hz, 1H), 7.10-7.35 (br.s., 1H), 7.37 (d, J=4.0 Hz, 1H).

Aufarbeitung

  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:PA=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-d64b9ca59a8e4e949e654aa1e85e3f50
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422244B2

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