Ammonium Chloride → Ethyl 3-benzyl-2-methyl-3,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate

HRID 453583Notes

Reaction equation

HRID 453583 reaction equation
[O-]CC.[Na+].[CH2:5]([N:12]1[CH:16]=[C:15]([CH:17]=O)[N:14]=[C:13]1[CH3:19])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[N+]=[N-].[Cl-].[NH4+]>C(O)C>[CH2:5]([N:12]1[C:16]2[NH:20][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:17][C:15]=2[N:14]=[C:13]1[CH3:19])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 69480Acetic acid, azido-, ethyl esterHCID 2723922Sodium ethoxideHCID 136062421-Benzyl-2-methylimidazole-4-carboxaldehyde

Product 1

HCID 24880659Ethyl 3-benzyl-2-methyl-3,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylateYield 6.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution (50 mL) of sodium ethoxide (5.4 g) in ethanol was added dropwise a mixture of 1-benzyl-2-methyl-1H-imidazole-4-carbaldehyde (3.8 g) and ethyl azidoacetate (10.3 g) under ice-cooling. After the completion of the dropwise addition, the mixture was stirred for 1 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was concentrated. The obtained residue was extracted with ethyl acetate. The ethyl acetate layer was is washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was dissolved in toluene (50 mL), and the mixture was stirred at 110° C. for 2 hr. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography to give ethyl 3-benzyl-2-methyl-3,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate (0.35 g, yield 6.5%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). melting point 193° C.

Workup

  1. temperaturecooling
  2. additionAfter the completion of the dropwise addition
  3. concentrationthe mixture was concentrated
  4. extractionThe obtained residue was extracted with ethyl acetate
  5. washThe ethyl acetate layer was is washed with saturated brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. dissolutionThe obtained residue was dissolved in toluene (50 mL)
  9. stirringthe mixture was stirred at 110° C. for 2 hr
  10. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-5bf680f8090a435c869eaa7326e732ca
Source dataset
uspto-grants-2013_07
Patent number
US08492405B2

Reaction notes

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