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

HRID 11984
Notes
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Reaction equation

HRID 11984 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-d73a86df4d0d4a32a23007aeff1a94e4
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
USRE041366E1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes