Reaction #56501

Reaction equation

methanesulfonylisocyanate

4-{3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic acid

triethylamine

→

N-Methylsulfonyl-4-{3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzamide

Solvents

acetonitrile

acetonitrile

Conditions

Workup

1. 1
   Otherevaporated at reduced pressure
2. 2
   workup.ADDITIONThe residue is treated with water
3. 3
   ExtractionThe crude product is extracted into chloroform
4. 4
   Otherpurified by chromatography on a silica gel column with elution by 4% methanol in chloroform

Procedure

A solution of methanesulfonylisocyanate (1.33 g., 0.011 mole) in acetonitrile (10 ml.) is added dropwise during 10 minutes to a solution of 4-{3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic acid (3.9 g., 0.01 mole) and triethylamine (1.0 g., 0.01 mole) in acetonitrile (30 ml.). The resulting solution is stored at 25° C. for 4 hours and then evaporated at reduced pressure. The residue is treated with water. The crude product is extracted into chloroform and purified by chromatography on a silica gel column with elution by 4% methanol in chloroform.

Source