5-Isopropyl-1,3,4-thiadiazol-2-amine → Acetic acid 4-(5-isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl ester

HRID 604458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604458
Cl[S:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH:15]([C:18]1[S:22][C:21]([NH2:23])=[N:20][N:19]=1)([CH3:17])[CH3:16]>N1C=CC=CC=1>[CH:15]([C:18]1[S:22][C:21]([NH:23][S:2]([C:5]2[CH:10]=[CH:9][C:8]([O:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=2)(=[O:4])=[O:3])=[N:20][N:19]=1)([CH3:17])[CH3:16]

Komponenten

4

Edukt 2

HCID 1471515-Isopropyl-1,3,4-thiadiazol-2-amineHCID 129257104-(Chlorosulfonyl)phenyl acetate

Produkt 1

HCID 57543180Acetic acid 4-(5-isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl esterAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

4.1 g acetic acid 4-chlorosulfonyl-phenyl ester were added to a stirred solution of 2.5 g 5-isopropyl-[1,3,4]thiadiazol-2-ylamine in 35 ml pyridine. The reaction mixture was stirred at room temperature overnight. The pyridine was removed in vacuo and the residue dissolved in 200 ml dichloromethane and washed with 60 ml water. The organic layer was dried over MgSO4. Then the solvent was removed in vacuo and the resulting residue purified by flash chromatography on silica gel with the eluents n-heptane:ethyl acetate=1:1=>1:3 to obtain 4.47 g Acetic acid 4-(5-isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl ester impurified with 40% of the byproduct N-(5-Isopropyl-[1,3,4]thiadiazol-2-yl)-acetamide. The material was used without further purification.

Aufarbeitung

  1. customThe pyridine was removed in vacuo
  2. dissolutionthe residue dissolved in 200 ml dichloromethane
  3. washwashed with 60 ml water
  4. dry with materialThe organic layer was dried over MgSO4
  5. customThen the solvent was removed in vacuo
  6. customthe resulting residue purified by flash chromatography on silica gel with the eluents n-heptane

Quellen und Nachweise

ORD-Eintrag
ord-8dd9fb98e8ba41b18ab82ddcaa4910b0
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910612B2

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