반응 #2467993

반응 방정식

sodium methoxide

sodium sulfide

3-chloro-3-phenylprop-2-enenitrile

chloroacetonitrile

→

solid

수율 8.0%

3-Amino-5-phenylthiophene-2-carbonitrile

수율 8.0%

용매

water

methanol

DMF

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGagain stirred at 60-70° C. for 2 h
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued for 1 h at the same temperature
4. 4
   기타was allowed to rt
5. 5
   workup.STIRRINGstirred for 15 min
6. 6
   기타The solid separated
7. 7
   여과was filtered
8. 8
   세척washed with water
9. 9
   기타dried
10. 10
    기타The solid was recrystallized from hexane-chloroform

실험 절차

To a suspension of sodium sulfide (0.95 g, 12.23 mmol) in DMF (12.5 mL) was added a solution of 3-chloro-3-phenylprop-2-enenitrile (2 g, 12.23 mmol) in DMF (5 mL) at rt for 5 min and stirred the mixture at 60-70° C. for 2 h. Then chloroacetonitrile (0.77 mL, 12.23 mmol) was added dropwise to the reaction mixture and again stirred at 60-70° C. for 2 h. Then, a solution of sodium methoxide (0.66 g, 12.23 mmol) in methanol (5 mL) was added dropwise and stirring was continued for 1 h at the same temperature. The mixture was allowed to rt and poured into cold water and stirred for 15 min. The solid separated was filtered, washed with water and dried. The solid was recrystallized from hexane-chloroform to give the product as a pale brown color solid (150 mg, 8%), nip 158-160° C. 1H NMR (400 MHz, CDCl3): δ 7.52-7.54 (2H, m), 7.37-7.41 (3H, m), 6.75 (1H, s), 4.48 (2H, s); LC-MS (negative ion mode): m/z 199 (M−H)−.

출처