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

HRID 11984

반응식

HRID 11984 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-d73a86df4d0d4a32a23007aeff1a94e4
출처 데이터셋
uspto-grants-2010_06
특허 번호
USRE041366E1

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