Toluene → HCID 21916117, compound

HRID 1349410Notes

Reaction equation

HRID 1349410 reaction equation
C(O[C:4]([C:6]1[N:10]2[CH2:11][CH2:12][N:13]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])[C:9]2=[N:8][C:7]=1[CH2:23][CH3:24])=[O:5])C.[CH2:25]([Mg]Cl)[CH2:26][CH3:27].[C:30]1(C)[CH:35]=CC=C[CH:31]=1>O1CCCC1>[CH2:23]([C:7]1[N:8]=[C:9]2[N:13]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])[CH2:12][CH2:11][N:10]2[C:6]=1[C:4]([OH:5])([CH2:31][CH2:30][CH3:35])[CH2:25][CH2:26][CH3:27])[CH3:24]

Participants

5

Reactant 3

HCID 1140TolueneHCID 20780236HCID 20780236, compoundHCID 178455855HCID 178455855, compound

Product 1

HCID 21916117HCID 21916117, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 2-ethyl-7-(2,4,6-trimethyl-phenyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carboxylic acid ethyl ester (1 mL of a 0.14 M solution in toluene) in tetrahydrofuran (1 mL) was added n-propylmagnesium chloride (0.84 mL of 1.0 M in tetrahydrofuran). The resulting solution was removed from the ice bath and allowed to stir for 15 min. It was then heated at reflux for 14 h. Upon cooling to room temperature, the reaction solution was quenched with saturated aqueous ammonium chloride, and the phases were separated. The aqueous phase was extracted twice with ether, and the combined organic portions were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give a yellow semi-solid (0.0448 g, 86%). LC/MS: tR=1.58 min., (MH+)=370.31.

Workup

  1. customThe resulting solution was removed from the ice bath
  2. temperatureIt was then heated
  3. temperatureat reflux for 14 h
  4. customthe reaction solution was quenched with saturated aqueous ammonium chloride
  5. customthe phases were separated
  6. extractionThe aqueous phase was extracted twice with ether
  7. washthe combined organic portions were washed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-56e3c24b5e8c477085a72bc5c5ac0f3d
Source dataset
uspto-grants-2007_05
Patent number
US07211669B2

Reaction notes

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