Isopropyl Isothiocyanate → N-[5-Chloro-3-(isopropylthiocarbamoyl)sulfamoylthiophen-2-yl]acetamide

HRID 1975925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1975925
CC(C)([O-])C.[K+].[Cl:7][C:8]1[S:12][C:11]([NH:13][C:14](=[O:16])[CH3:15])=[C:10]([S:17](=[O:20])(=[O:19])[NH2:18])[CH:9]=1.[CH:21]([N:24]=[C:25]=[S:26])([CH3:23])[CH3:22]>CN(C)C=O>[Cl:7][C:8]1[S:12][C:11]([NH:13][C:14](=[O:16])[CH3:15])=[C:10]([S:17](=[O:19])(=[O:20])[NH:18][C:25](=[S:26])[NH:24][CH:21]([CH3:23])[CH3:22])[CH:9]=1

Komponenten

5

Edukt 3

HCID 75263Isopropyl IsothiocyanateHCID 22000000N-(5-chloro-3-sulfamoylthiophen-2-yl)-acetamideHCID 23665647Potassium tert-butoxide2×

Produkt 1

HCID 21999986N-[5-Chloro-3-(isopropylthiocarbamoyl)sulfamoylthiophen-2-yl]acetamideAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Potassium tert-butoxide (135 mg, 1.2 mmol) was added to a solution of N-(5-chloro-3-sulfamoylthiophen-2-yl)-acetamide(255 mg, 1.0 mmol) in dry N,N-dimethylformamide (5 ml) with stirring on an ice bath. After 5 min, isopropyl isothiocyanate (0.128 ml, 1.2 mmol) was added dropwise and the solution was stirred for 30 min at 0° C. and then at room temperature for 3 h. A further amount of potassium tert-butoxide (135 mg, 1.2 mmol) was added to the solution and stirring was continued at room temperature for 1 h. The solvent was evaporated at <50° C., and the residue was taken up in 10 ml of water and the aqueous solution was adjusted to pH 2 with 4 M hydrochloric acid. The resulting precipitate was isolated by filtration, washed with water and dried to give 274 mg (77%) of crude title compound; 1H-NMR (DMSO-d6): δ1.12 (d, 6H, 2×CH3), 2.28 (s, 3H, COCH3), 4.21 (m, 1H, NCH), 7.15 (s, 1H, H-4), 8.34 (br d, 1H, NH), 10.26 (s, 1H, NH).

Aufarbeitung

  1. stirringthe solution was stirred for 30 min at 0° C.
  2. waitat room temperature for 3 h
  3. stirringstirring
  4. waitwas continued at room temperature for 1 h
  5. customThe solvent was evaporated at <50° C.
  6. customThe resulting precipitate was isolated by filtration
  7. washwashed with water
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-02047be2713242a895c4f00e30bfd6a9
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06225310B1

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