Chloroform → 3-cyclopropyl-2-(4-methoxy-phenyl)-3H-imidazole-4-carbaldehyde

HRID 732103Notes

Reaction equation

HRID 732103 reaction equation
[CH:1]1([NH:4][C:5](=[NH:14])[C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.Br[C:16](=[CH:19]OC(C)C)[CH:17]=[O:18].C([O-])([O-])=O.[K+].[K+].C(Cl)(Cl)Cl>O>[CH:1]1([N:4]2[C:16]([CH:17]=[O:18])=[CH:19][N:14]=[C:5]2[C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 534166342-Bromo-3-isopropoxy-propenalHCID 178491237HCID 178491237, compound

Product 1

HCID 578380093-cyclopropyl-2-(4-methoxy-phenyl)-3H-imidazole-4-carbaldehydeYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-cyclopropyl-4-methoxy-benzamidine (0.90 g, 4.75 mmol), 2-bromo-3-isopropoxy-propenal (1.37 g, 7.12 mmol) and K2CO3 (0.98 g, 7.12 mmol) were mixed with chloroform (10 ml) and water (1.2 ml), followed by stirring at r.t. for 24 h. After drying of the reaction mixture (Na2SO4), filtration and concentration of the filterate in-vacuo, the crude residue was purified via flash chromatography (40% EA in hex.) to isolate the title compound (973 mg, 85%). 1H-NMR: 9.83 (s, 1H), 7.82 (m, 3H), 7.02 (d, 2H), 3.89 (s, 3H), 3.58 (m, 1H), 1.13 (m, 2H), 0.64 (m, 2H).

Workup

  1. dry with materialAfter drying of the reaction mixture (Na2SO4), filtration and concentration of the filterate in-vacuo
  2. customthe crude residue was purified via flash chromatography (40% EA in hex.)

Sources & evidence

ORD record
ord-59d3df64d5184e9fb6ce967002974f67
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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