반응 #1908186

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N′-(3-cyano-4-isopropyloxyphenylcarbonyl)-4-bromo-2-methylbenzhydrazide

N′-(3-Cyano-4-isopropyloxyphenylcarbonyl)-4-bromo-2-methylbenzhydrazide

toluene

Lawesson's Reagent

→

title compound

2-(3-Cyano-4-isopropyloxy-phenyl)-5-(4-bromo-2-methyphenyl)-1,3,4-thiadiazole

용매

pyridine

반응 조건

후처리

1. 1
   기타cap
2. 2
   온도The resulting mixture was cooled down to rt
3. 3
   기타solvents were removed under reduced pressure and residual solids
4. 4
   workup.DISSOLUTIONwere dissolved in 10 mL of pyridine
5. 5
   workup.ADDITIONTo this mixture, 0.5 g of phosphorous pentasulfide was added
6. 6
   온도the mixture heated to 110° C
7. 7
   추출extracted 2×100 mL of EtOAc
8. 8
   건조Combined organic layers were dried over sodium sulfate, and solvents
9. 9
   기타removed under reduced pressure

실험 절차

In an oven-dried high-pressure tube, 240 mg (0.58 mmol) of N′-(3-cyano-4-isopropyloxyphenylcarbonyl)-4-bromo-2-methylbenzhydrazide (from Step A) was combined with 40 mL of anhydrous toluene, 300 mg of Lawesson's Reagent (0.74 mmol), and 100 μL of pyridine. The tube was sealed with a plastic/teflon cap and the reaction mixture was heated to 125° C. for 2 h. The resulting mixture was cooled down to rt, solvents were removed under reduced pressure and residual solids were dissolved in 10 mL of pyridine. To this mixture, 0.5 g of phosphorous pentasulfide was added and the mixture heated to 110° C. The reaction mixture was combined with ice-water and extracted 2×100 mL of EtOAc. Combined organic layers were dried over sodium sulfate, and solvents removed under reduced pressure. Pure title compound was isolated by flash chromatography using Biotage 40S (eluant: hexanes/EtOAc-4/1) to yield 239 mg: 1H NMR (500 MHZ, CDCl3) δ 1.49 (d, J=6.5, 6H), 2.65 (s, 3H), 4.79 (sep, J=6.5, 1H), 7.13 (dd, J=9.0, 2.0, 1H), 7.50 (dd, J=9.0, 2.0, 1H), 7.56 (d, J=2.0, 1H), 7.63 (d, J=8.0, 1H), 8.17 (d, J=2.0, 1H), 8.24 (dd, J=8.0, 2.0, 1H).

출처