تفاعل #2467995

معادلة التفاعل

3-amino-5-phenylthiophene-2-carboxamide

sodium nitrite

→

solid

المردود 51.3%

6-Phenyl-3H-thiopheno[3,2-d]1,2,3-triazin-4-one

المردود 51.3%

المذيبات

sulfuric acid

sulfuric acid

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwhile adding
2. 2
   أخرىshould keep between −5-0° C.
3. 3
   workup.ADDITIONAfter addition
4. 4
   درجة الحرارةThe reaction mixture was cooled
5. 5
   workup.ADDITIONpoured
6. 6
   أخرىinto crushed ice slowly
7. 7
   workup.STIRRINGwith stirring for 15 min
8. 8
   workup.STIRRINGstirred at the same temperature for 15 min
9. 9
   استخلاصThe solution was extracted with ethyl acetate (3×50 mL)
10. 10
    غسيلthe combined EtOAc layer was washed with water, brine
11. 11
    تجفيفdried over sodium sulfate
12. 12
    ترشيحThe solution was filtered
13. 13
    أخرىevaporated the solvent

الإجراء التجريبي

To an ice cold solution (0° C.) of 3-amino-5-phenylthiophene-2-carboxamide (0.37 g, 1.7 mmol) in concentrated sulfuric acid (20 mL) was added a cold (0° C.) solution of sodium nitrite (120 mg, 1.86 mmol) in concentrated sulfuric acid (8 mL) for 10 min (while adding, the temperature should keep between −5-0° C.). After addition, the mixture was stirred at 0° C. for 1 h and at rt for 1 h. The reaction mixture was cooled and poured into crushed ice slowly with stirring for 15 min and stirred at the same temperature for 15 min. The solution was extracted with ethyl acetate (3×50 mL) and the combined EtOAc layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent to give the product as an off-white color solid (200 mg, 39%), my 178-180° C. 1H NMR (400 MHz, CDCl3): δ 12.30 (1H, br s), 7.86 (1H, s), 7.73-7.75 (2H, m), 7.49-7.54 (3H, m); LC-MS (negative ion mode): m/z 228 (M−H)−.

المصدر