Water → 2-(3-Methoxybenzylthio)nicotinic acid

HRID 35529Notes

Reaction equation

HRID 35529 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 8593402-(3-Methoxybenzylthio)nicotinic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6f633874bdd242acb222fcad7b159dc6
Source dataset
uspto-grants-1988_08
Patent number
US04767766

Reaction notes

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