Dimethyl Sulfoxide → 2-(4-Isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-6-methyl-5-methylthiomethoxy-nicotinic acid methyl ester

HRID 329434Notes

Reaction equation

HRID 329434 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([OH:10])[C:7]([CH3:11])=[N:6][C:5]=1[C:12]1[NH:13][C:14](=[O:21])[C:15]([CH:18]([CH3:20])[CH3:19])([CH3:17])[N:16]=1.[H-].[Na+].[CH3:25][S:26]([CH3:28])=O>>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([O:10][CH2:25][S:26][CH3:28])[C:7]([CH3:11])=[N:6][C:5]=1[C:12]1[NH:13][C:14](=[O:21])[C:15]([CH:18]([CH3:20])[CH3:19])([CH3:17])[N:16]=1

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 1363428005-Hydroxy-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-6-methyl-nicotinic acid methyl ester

Product 1

HCID 137994192-(4-Isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-6-methyl-5-methylthiomethoxy-nicotinic acid methyl ester

Procedure

A solution of 2.5 g (8.19 mmol) 5-hydroxy-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-6-methyl-nicotinic acid methyl ester in 25 ml dimethyl sulfoxide is reacted with 0.26 g (8.19 mmol) sodium hydride (80%) and after 10 minutes' stirring, 0.87 g (9.01 mmol) chlorodimethylsulfide is added. It is stirred overnight, then added to 500 ml ice water. The product is extracted with ethyl acetate, the extract is dried over magnesium sulfate, and compressed. The residue is chromatographed over silica gel with ethyl acetate/hexane 1:1.

Workup

  1. stirringIt is stirred overnight
  2. extractionThe product is extracted with ethyl acetate
  3. dry with materialthe extract is dried over magnesium sulfate
  4. customThe residue is chromatographed over silica gel with ethyl acetate/hexane 1:1

Sources & evidence

ORD record
ord-953c349e4aeb42a4a50f5088b2703a9f
Source dataset
uspto-grants-1990_01
Patent number
US04891428

Reaction notes

Loading…