Reaction #487550

Reaction equation

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

4-chloro-butyryl chloride

potassium carbonate

→

required product

Yield 85.2%

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

Yield 85.2%

Solvents

toluene

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureunder reflux for 4 hr
3. 3
   OtherThe toluene was then evaporated under reduced pressure
4. 4
   OtherThe residue was then quenched with water
5. 5
   Filtrationfiltered
6. 6
   OtherThe solid obtained
7. 7
   Washwas washed
8. 8
   Otherdried
9. 9
   Otherrecrystallized from toluene

Procedure

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.

Source