Reaction #56528

Reaction equation

sodium 3-acetamido-2,4,6-triiodobenzoate

chloromethyl ethyl ether

→

product

Yield 32.8%

Ethoxymethyl 3-Acetamido-2,4,6-triiodobenzoate

Yield 32.8%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   OtherA white solid (NaCl) precipitated promptly
2. 2
   Filtrationfiltered
3. 3
   Otherevaporated
4. 4
   Otherto yield 17.8 g
5. 5
   workup.DISSOLUTIONThe residue was dissolved in 200 ml
6. 6
   Filtrationof chloroform, filtered
7. 7
   Extractionthe filtrate was extracted with 5% aqueous sodium bicarbonate
8. 8
   Washwashed with water
9. 9
   Dryingdried over anhydrous sodium sulfate
10. 10
    Otherevaporated under reduced pressure to dryness
11. 11
    OtherThe residue (10.5 g.) obtained
12. 12
    Otherwas recrystallized from carbon tetrachloride (200 ml.) and chloroform (enough
13. 13
    workup.DISSOLUTIONto dissolve the residue),

Procedure

To a stirred slurry of sodium 3-acetamido-2,4,6-triiodobenzoate (14.5 g, 0.025 mole) in dimethylformamide (150 ml) was added chloromethyl ethyl ether (2.56 g, 0.027 mole). A white solid (NaCl) precipitated promptly. The mixture was stirred overnight, filtered, and evaporated to near dryness under reduced pressure to yield 17.8 g. of residue. The residue was dissolved in 200 ml. of chloroform, filtered and the filtrate was extracted with 5% aqueous sodium bicarbonate, washed with water and dried over anhydrous sodium sulfate and evaporated under reduced pressure to dryness. The residue (10.5 g.) obtained was recrystallized from carbon tetrachloride (200 ml.) and chloroform (enough to dissolve the residue), to yield the product 5.05 g. (31.5%), m.p. 174°-177.7° C. The ir and and nmr spectra were in agreement with the structure as assigned.

Source