تفاعل #487550

معادلة التفاعل

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

4-chloro-butyryl chloride

potassium carbonate

→

required product

المردود 85.2%

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

المردود 85.2%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated
2. 2
   درجة الحرارةunder reflux for 4 hr
3. 3
   أخرىThe toluene was then evaporated under reduced pressure
4. 4
   أخرىThe residue was then quenched with water
5. 5
   ترشيحfiltered
6. 6
   أخرىThe solid obtained
7. 7
   غسيلwas washed
8. 8
   أخرىdried
9. 9
   أخرىrecrystallized from toluene

الإجراء التجريبي

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.

المصدر