反応 #56528

反応方程式

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

chloromethyl ethyl ether

→

product

収率 32.8%

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

収率 32.8%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   その他A white solid (NaCl) precipitated promptly
2. 2
   ろ過filtered
3. 3
   その他evaporated
4. 4
   その他to yield 17.8 g
5. 5
   workup.DISSOLUTIONThe residue was dissolved in 200 ml
6. 6
   ろ過of chloroform, filtered
7. 7
   抽出the filtrate was extracted with 5% aqueous sodium bicarbonate
8. 8
   洗浄washed with water
9. 9
   乾燥dried over anhydrous sodium sulfate
10. 10
    その他evaporated under reduced pressure to dryness
11. 11
    その他The residue (10.5 g.) obtained
12. 12
    その他was recrystallized from carbon tetrachloride (200 ml.) and chloroform (enough
13. 13
    workup.DISSOLUTIONto dissolve the residue),

実験手順

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.

出典