Water → 2-(3-Methoxybenzylthio)nicotinic acid

HRID 1200003

Reaktionsgleichung

Reaktionsgleichung von HRID 1200003
[SH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C[O-].[Na+].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19]Cl.O>CO>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][S:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Komponenten

6

Edukt 4

HCID 962WaterHCID 699943-Methoxybenzyl chlorideHCID 10942334Sodium MethoxideHCID 178524460HCID 178524460, Verbindung

Produkt 1

HCID 8593402-(3-Methoxybenzylthio)nicotinic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A suspension of 4.65 g (0.03 mole) of 2-mercaptonicotinic acid in 100 ml of methanol was cooled in ice as 3.24 g (0.06 mole) of sodium methoxide was added. The resulting solution was left at ice-temperature as 4.68 g (0.03 mole) of 3-methoxybenzyl chloride was added over 5 minutes. The reaction mixture was stirred for 14 hours and the reaction set solid. The addition of 50 ml of water caused solution and an excess of acetic acid precipitated 7.55 g (92% of theory) of 2-(3-methoxybenzylthio)nicotinic acid. Recrystallization was effected from ethyl acetate; m.p. 156°-157° C.

Aufarbeitung

  1. additionwas added
  2. additionwas added over 5 minutes
  3. customan excess of acetic acid precipitated 7.55 g (92% of theory) of 2-(3-methoxybenzylthio)nicotinic acid
  4. customRecrystallization

Quellen und Nachweise

ORD-Eintrag
ord-74d1489dc642434693864f66287c65c9
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04904672

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