Toluene → HCID 21916117, compound

HRID 1293069Notes

Reaction equation

HRID 1293069 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 0.14M solution in toluene) in tetrahydrofuran (1 mL) was added n-propylmagnesium chloride (0.84 mL of 1.0M 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-d7a3ec4008164454b32dab6d063bd9e6
Source dataset
uspto-grants-2007_07
Patent number
US07238699B2

Reaction notes

Loading…