Reaktion #487550

Reaktionsgleichung

5-phenyl-1,3,4-thiadiazol-2-amine

4-chloro-butyryl chloride

potassium carbonate

→

required product

Ausbeute 85.2%

4-Chloro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)butanamide

Ausbeute 85.2%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux for 4 hr
3. 3
   SonstigeThe toluene was then evaporated under reduced pressure
4. 4
   SonstigeThe residue was then quenched with water
5. 5
   Filtrationfiltered
6. 6
   SonstigeThe solid obtained
7. 7
   Waschenwas washed
8. 8
   Sonstigedried
9. 9
   Sonstigerecrystallized from toluene

Vorschrift

A mixture of 5-phenyl-1,3,4-thiadiazol-2-amine (7.1 g, 0.04 mol), 4-chloro-butyryl chloride (11.3 g, 9.0 ml, 0.08 mol) and potassium carbonate (5.5 g, 0.04 mole) in toluene (100 ml) was heated under reflux for 4 hr. The toluene was then evaporated under reduced pressure. The residue was then quenched with water, stirred, and filtered. The solid obtained was washed, dried and recrystallized from toluene to give the required product (9.6 g, 85% yield), mp 159-62° C., m/e 281, 87% (consistent with molecular formula C12H12ClN3OS, calcd. 281.04). 1H NMR (DMSO-d6): δ 2.07-2.10 (m, 2H, —CH2), 2.67-2.70 (m, 2H, —CH2), 3.70-3.72 (m, 2H, —CH2), 7.48-7.54 (m, 3H, ArH), 7.93-7.94 (m, 2H, ArH), 12.65 (br s, 1H, NH). 13C NMR: δ 27.9, 32.7, 45.1, 127.4, 129.8, 130.7, 131.0, 158.5, 162.4, 171.2.

Quelle