반응 #487550

반응 방정식

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

4-chloro-butyryl chloride

potassium carbonate

→

required product

수율 85.2%

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

수율 85.2%

용매

toluene

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도under reflux for 4 hr
3. 3
   기타The toluene was then evaporated under reduced pressure
4. 4
   기타The residue was then quenched with water
5. 5
   여과filtered
6. 6
   기타The solid obtained
7. 7
   세척was washed
8. 8
   기타dried
9. 9
   기타recrystallized from toluene

실험 절차

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.

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