تفاعل #364171

معادلة التفاعل

water

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

Lawesson's reagent

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product

المردود 90.5%

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

المردود 90.5%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was cooled to room temperature
2. 2
   استخلاصextracted with ethyl acetate (2×100 mL)
3. 3
   غسيلwashed with brine (50 mL)
4. 4
   تجفيفdried over magnesium sulfate
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىPurification by flash column chromatography on silica gel

الإجراء التجريبي

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.

المصدر