반응 #9413

반응 방정식

water

5-(2′-oxospiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-1-methyl-pyrrole-2-carbonitrile

Lawesson's reagent

→

product

수율 90.5%

5-(2′-THIOXOSPIRO[CYCLOHEXANE-1,3′-[3H]INDOL]-5′-YL)-1-METHYL-PYRROLE-2-CARBONITRILE

수율 90.5%

용매

toluene

반응 조건

후처리

1. 1
   온도The reaction was cooled to room temperature
2. 2
   추출extracted with ethyl acetate (2×100 mL)
3. 3
   세척washed with brine (50 mL)
4. 4
   건조dried over magnesium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타Purification by flash column chromatography on silica gel

실험 절차

To a solution of 5-(2′-oxospiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-1-methyl-pyrrole-2-carbonitrile (0.55 g, 1.8 mmol, 1 eq) in toluene (50 mL) was added Lawesson's reagent (0.47 g, 1.1 mmol, 0.65 eq) and the reaction was heated to 80° C. for 1 hour. The reaction was cooled to room temperature, poured into water (100 mL) and extracted with ethyl acetate (2×100 mL). The organic layers were combined, washed with brine (50 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by flash column chromatography on silica gel gave the product as a white solid (0.32 g, 55%). 1H NMR (d6-DMSO, 500 MHz) δ 1.36–1.99 (m, 10 H), 3.7 (s, 3 H), 6.35 (d, 1 H, J=4.2 Hz), 7.05 (d, 1 H, J=4.2 Hz), 7.16 (d, 1 H, J=7.9 Hz), 7.44 (dd, 1 H, J=1.6, 8.1 Hz), 7.83 (d, 1 H, J=1.6 Hz), 12.75 (s, 1 H). MS (ESI) [M−H]−=320. Anal. calcd. for C19H19N3S: C, 70.99; H, 5.96; N, 13.07. Found: C, 68.69; H, 5.36; N, 12.27.

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