Reaktion #63822

Reaktionsgleichung

4-(4-methoxybenzylthio)-nicotinic acid

1,1'-carbonyldiimidazole

sodium methoxide

→

Methyl 4-(4-methoxybenzylthio)nicotinate

Lösungsmittel

methanol

N,N-dimethylformamide

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction was stirred for 1 hour at room temperature
2. 2
   Sonstigepartitioned between 75 mL of ether and 30 mL of water
3. 3
   ExtraktionThe ether layer was extracted with 2×30 mL of water
4. 4
   Sonstigedried
5. 5
   Einengenconcentrated to a small volume, and hexane
6. 6
   workup.ADDITIONadded
7. 7
   Sonstigeto crystallize methyl 4-(4-methoxybenzylthio) nicotinate

Vorschrift

A suspension of 2.2 g (0.008 mole) of 4-(4-methoxybenzylthio)-nicotinic acid in 30 mL of dry N,N-dimethylformamide was reacted with 1.78 g (0.011 mole) of 1,1'-carbonyldiimidazole. This was stirred at room temperature for 2 hours, then 0.5 mL of 4.3M sodium methoxide in methanol and 5 mL of methanol. The reaction was stirred for 1 hour at room temperature, then partitioned between 75 mL of ether and 30 mL of water. The ether layer was extracted with 2×30 mL of water, dried, concentrated to a small volume, and hexane added to crystallize methyl 4-(4-methoxybenzylthio) nicotinate; yield 1.66 g (72% of theory), m.p. 108°-110° C.

Quelle