Reaction #84802

Reaction equation

methyl 2-(4-aminophenyl)-2-methoxyacetate

3-chloropropane-1-sulfonyl chloride

→

methyl 2-(4-(3-chloropropylsulfonamido)phenyl)-2-methoxyacetate

Yield 99.9%

Solvents

pyridine

H2O

HCl

brine

Conditions

Workup

1. 1
   OtherThe exothermic reaction
2. 2
   Temperaturewas cooled briefly over a cold H2O bath
3. 3
   Extractionextracted with EtOAc
4. 4
   WashThe combined organics were washed with 1 M HCl, H2O and brine
5. 5
   Dryingthen dried over Na2SO4
6. 6
   Concentrationconcentrated in vacuo

Procedure

To a solution of methyl 2-(4-aminophenyl)-2-methoxyacetate (0.6 g, 3.07 mmol) in anhydrous pyridine (6 mL) under argon was added 3-chloropropane-1-sulfonyl chloride (0.5 mL, 4.11 mmol) dropwise. The exothermic reaction was cooled briefly over a cold H2O bath. After stirring for 1 hr, the reaction was diluted with H2O, 1 M HCl and brine and extracted with EtOAc. The combined organics were washed with 1 M HCl, H2O and brine then dried over Na2SO4 and concentrated in vacuo to give methyl 2-(4-(3-chloropropylsulfonamido)phenyl)-2-methoxyacetate as an orange oil (1.03 g, quant. yield). The product was used without further purification.

Source