Methyl iodide → Methyl 2-(3-methoxybenzylthio)nicotinate

HRID 1200004Notes

Reaction equation

HRID 1200004 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][S:7][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].[CH3:20]I>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][S:7][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([O:12][CH3:20])=[O:11]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 8593402-(3-Methoxybenzylthio)nicotinic acid

Product 1

HCID 14277645Methyl 2-(3-methoxybenzylthio)nicotinateYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 7.15 g (0.026 mole) of 2-(3-methoxybenzylthio)nicotinic acid in 75 ml of dry acetonitrile was treated with 3.95 g (0.026 mole) of 1,8-diazabicyclo[5,4,0]-under-7-ene (DBU). A solution formed and 4.26 g (0.030 mole) of methyl iodide was added over one minute. After keeping the reaction mixture at room temperature for 24 hours, the solution was evaporated in vacuo. The residue was partitioned between 100 ml of ether and 50 ml of water. The ether layer was washed with 50 ml of H2O, dried, and evaporated to a small volume. The addition of hexane with cooling yielded 6.9 g (92% of theory) of methyl 2-(3-methoxybenzylthio)nicotinate; m.p. 69°-70° C.

Workup

  1. customA solution formed
  2. customat room temperature
  3. customfor 24 hours
  4. customthe solution was evaporated in vacuo
  5. customThe residue was partitioned between 100 ml of ether and 50 ml of water
  6. washThe ether layer was washed with 50 ml of H2O
  7. customdried
  8. customevaporated to a small volume
  9. additionThe addition of hexane
  10. temperaturewith cooling

Sources & evidence

ORD record
ord-4c7eadf0d4634414b90c69607db25147
Source dataset
uspto-grants-1990_02
Patent number
US04904672

Reaction notes

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