4-Methoxy-alpha-toluenethiol → Methyl 3-[[(4-methoxyphenyl)methyl]thio]-2-pyridinecarboxylate

HRID 1084745Notes

Reaction equation

HRID 1084745 reaction equation
CNN(NC)[C:4]([S:6][C:7]1[C:8]([C:13]([O:15][CH3:16])=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=1)=O.CO.C[O-].[Na+].[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29](CS)=[CH:28][CH:27]=1>CO>[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:4][S:6][C:7]2[C:8]([C:13]([O:15][CH3:16])=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 804074-Methoxy-alpha-toluenethiolHCID 23694274Sodium methanolate methanolHCID 86742402methyl 3-(N,N-dimethylaminocarbamoylthio)pyridine-2-carboxylate

Product 1

HCID 14277622Methyl 3-[[(4-methoxyphenyl)methyl]thio]-2-pyridinecarboxylateYield 62.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.20 g (5 mmol) of methyl 3-(N,N-dimethylaminocarbamoylthio)pyridine-2-carboxylate in 5 mL of methanol and 1.5 mL (6 mmol) of 4.lM sodium methoxide methanol was stirred at room temperature for 10 minutes. Then the solvent was concentrated and the residue was dissolved in 5 mL of N,N-dimethylformamide and 5 mL of tetrahydrofuran. 0.936 g (6 mmol) of p-methoxybenzylmercaptan was added and the solution was stirred at room temperature for 18 hours. The solution was partitioned between ether and water and the aqueous layer was extracted with two portions of ether. The combined extracts were washed with brine, dried and concentrated. Recrystallization from methanol afforded 0.90 g (62%) of pale tan needles, m.p. 99°-100° C.

Workup

  1. concentrationThen the solvent was concentrated
  2. dissolutionthe residue was dissolved in 5 mL of N,N-dimethylformamide
  3. customThe solution was partitioned between ether and water
  4. extractionthe aqueous layer was extracted with two portions of ether
  5. washThe combined extracts were washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customRecrystallization from methanol

Sources & evidence

ORD record
ord-471ca076e5854011bd88dfe4edb17758
Source dataset
uspto-grants-1991_04
Patent number
US05006532

Reaction notes

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