Triethylamine → 2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-(2'-iodo-6'-methoxyphenyl)acetamide

HRID 11984

反応式

HRID 11984 の反応式
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[I:15][C:16]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:17]=1[NH2:18].[I-].ClC1C=CC=C[N+]=1C.C(N(CC)CC)C>ClCCl>[O:4]1[C:5]2([CH2:10][CH2:9][C:8]([CH2:11][C:12]([NH:18][C:17]3[C:19]([O:23][CH3:24])=[CH:20][CH:21]=[CH:22][C:16]=3[I:15])=[O:14])=[CH:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 112870902-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)acetic acidHCID 113796632-Iodo-6-methoxyaniline

生成物 1

HCID 219516902-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-(2'-iodo-6'-methoxyphenyl)acetamide収率 89.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (1,4-dioxaspiro[4.5]dec-7-en-8-yl) acetic acid (567 mg; 2.86 mmol; 1 eq) (7) and 2-iodo-6-methoxyaniline (1 g; 2.86 mmol; 1 eq) in anhydrous dichloromethane (30 mL) is admixed with 2-chloro-1-methylpyridinium iodide (1.46 g; 5.73 mmol; 2 eq) and triethylamine (3.98 mL; 28.65 mmol; 10 eq). The reaction mixture is heated at reflux for 20 hours. After cooling and acidification with 1N HCl solution to pH=5-6, the mixture is extracted with dichloromethane. The organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and evaporated under vacuum. Purification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 4/6) gives 1.10 g of 2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-(2′-iodo-6′-methoxy-phenyl)acetamide (16) in the form of a yellow foam (yield: 90%).

後処理

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 20 hours
  3. temperatureAfter cooling
  4. extractionacidification with 1N HCl solution to pH=5-6, the mixture is extracted with dichloromethane
  5. washThe organic phases are washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under vacuum
  8. customPurification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 4/6)

出典と根拠

ORDレコード
ord-d73a86df4d0d4a32a23007aeff1a94e4
出典データセット
uspto-grants-2010_06
特許番号
USRE041366E1

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