Reaction #1126

Reaction equation

H2S

3-p-cyanophenyl-5-(p-methoxycarbonyimethylphenoxymethyl)oxazolidin-2-one

pyridine

→

3-p-amidinophenyl-5-(p-methoxycarbonylmethylphenoxymethyl)oxazolidin-2-one

Solvents

triethylamine

Conditions

Workup

1. 1
   Concentrationconcentrated by evaporation
2. 2
   workup.DISSOLUTIONthe residue is dissolved in 50 ml of acetone
3. 3
   workup.ADDITIONtreated with 9 ml of methyl iodide
4. 4
   workup.STIRRINGAfter this mixture has been stirred for a further 6 h
5. 5
   Filtrationit is filtered
6. 6
   Washthe residue is washed with 5 ml of acetone
7. 7
   workup.DISSOLUTIONdissolved in 30 ml of methanol
8. 8
   workup.ADDITION4.6 g of ammonium acetate are added to this solution, which
9. 9
   workup.STIRRINGis stirred at room temperature for 24 h

Procedure

H2S gas is passed, at -10°, into a solution of 1.2 g of 3-p-cyanophenyl-5-(p-methoxycarbonyimethylphenoxymethyl)oxazolidin-2-one (obtainable in accordance with Example 1) in 50 ml of pyridine and 7 ml of triethylamine. The mixture is subsequently stirred at room temperature for 14 h and concentrated by evaporation; the residue is dissolved in 50 ml of acetone and treated with 9 ml of methyl iodide. After this mixture has been stirred for a further 6 h, it is filtered and the residue is washed with 5 ml of acetone and dissolved in 30 ml of methanol; 4.6 g of ammonium acetate are added to this solution, which is stirred at room temperature for 24 h. Following the customary working-up, 3-p-amidinophenyl-5-(p-methoxycarbonylmethylphenoxymethyl)oxazolidin-2-one (semihydriodide) is obtained, M.p. 151°-152°.

Source