Chloromethyl ethyl ether → Ethoxymethyl 3-acetamido-2,4,6-triiodobenzoate

HRID 28250

反応式

HRID 28250 の反応式
[C:1]([NH:4][C:5]1[C:6]([I:16])=[C:7]([C:11]([I:15])=[CH:12][C:13]=1[I:14])[C:8]([O-:10])=[O:9])(=[O:3])[CH3:2].[Na+].[CH2:18]([O:20][CH2:21]Cl)[CH3:19]>CN(C)C=O>[C:1]([NH:4][C:5]1[C:6]([I:16])=[C:7]([C:11]([I:15])=[CH:12][C:13]=1[I:14])[C:8]([O:10][CH2:21][O:20][CH2:18][CH3:19])=[O:9])(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 18523Chloromethyl ethyl etherHCID 23665874Acetrizoate Sodium

生成物 1

HCID 12818238Ethoxymethyl 3-acetamido-2,4,6-triiodobenzoate収率 32.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

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.

後処理

  1. customA white solid (NaCl) precipitated promptly
  2. filtrationfiltered
  3. customevaporated
  4. customto yield 17.8 g
  5. dissolutionThe residue was dissolved in 200 ml
  6. filtrationof chloroform, filtered
  7. extractionthe filtrate was extracted with 5% aqueous sodium bicarbonate
  8. washwashed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customevaporated under reduced pressure to dryness
  11. customThe residue (10.5 g.) obtained
  12. customwas recrystallized from carbon tetrachloride (200 ml.) and chloroform (enough
  13. dissolutionto dissolve the residue),

出典と根拠

ORDレコード
ord-e44c934bbac048519108b55b15927ed8
出典データセット
uspto-grants-1980_09
特許番号
US04225725

関連ノート

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