반응 #2467995

반응 방정식

3-amino-5-phenylthiophene-2-carboxamide

sodium nitrite

→

solid

수율 51.3%

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

수율 51.3%

용매

sulfuric acid

sulfuric acid

반응 조건

후처리

1. 1
   workup.ADDITIONwhile adding
2. 2
   기타should keep between −5-0° C.
3. 3
   workup.ADDITIONAfter addition
4. 4
   온도The reaction mixture was cooled
5. 5
   workup.ADDITIONpoured
6. 6
   기타into crushed ice slowly
7. 7
   workup.STIRRINGwith stirring for 15 min
8. 8
   workup.STIRRINGstirred at the same temperature for 15 min
9. 9
   추출The solution was extracted with ethyl acetate (3×50 mL)
10. 10
    세척the combined EtOAc layer was washed with water, brine
11. 11
    건조dried over sodium sulfate
12. 12
    여과The solution was filtered
13. 13
    기타evaporated the solvent

실험 절차

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)−.

출처