反応 #487550

反応方程式

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

4-chloro-butyryl chloride

potassium carbonate

→

required product

収率 85.2%

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

収率 85.2%

溶媒

toluene

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度under reflux for 4 hr
3. 3
   その他The toluene was then evaporated under reduced pressure
4. 4
   その他The residue was then quenched with water
5. 5
   ろ過filtered
6. 6
   その他The solid obtained
7. 7
   洗浄was washed
8. 8
   その他dried
9. 9
   その他recrystallized from toluene

実験手順

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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