Ethyl 1-(N,N-dimethylsulfamoyl)-1H-imidazole-4-carboxylate → 4-(hydroxymethyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide
Reaction equation
[CH3:1][N:2]([CH3:16])[S:3]([N:6]1[CH:10]=[C:9]([C:11](OCC)=[O:12])[N:8]=[CH:7]1)(=[O:5])=[O:4].[H-].C([Al+]CC(C)C)C(C)C>>[OH:12][CH2:11][C:9]1[N:8]=[CH:7][N:6]([S:3](=[O:5])(=[O:4])[N:2]([CH3:1])[CH3:16])[CH:10]=1Participants
Procedure
Crude ethyl 1-(dimethylsulphamoyl)imidazole-4-carboxylate, from method 1, was reduced with diisobutylaluminium hydride to give 4-hydroxymethyl-1-(dimethylsulphamoyl)-imidazole. A mixture of this product (1.09 g) in methylene chloride (10 ml), dihydropyran (1.0 ml), pyridinium tosylate (1.26 g) and a few crystals of tosic acid was stirred at room temperature for 60 hours. Solvent was removed and the residue worked up to give 1-(dimethylsulphamoyl)-4-(tetrahydropyran-2-yloxy)imidazole, as an oil. This was cyanated with tosyl cyanide and butyllithium as described above to give 2-cyano-1-(dimethylsulphamoyl)-4-(tetrahydropyran-2-yloxy)imidazole, as an oil. A solution of this (150 mg) in ethanol (3 ml) was heated under reflux for 5 minutes after addition of a few milligrams of pyridinium tosylate. Solvent was removed and the residue purified by silica gel chromatography to give the starting material.
Sources & evidence
- ORD record
- ord-52005509e75c4a3ab643f376ecac2f3a
- Source dataset
- uspto-grants-1992_03
- Patent number
- US05096915
Reaction notes
Loading…