Chloroacetaldehyde → 1-(2,6-diisopropylphenyl)-2-(5-methoxy-[1,1'-biphenyl]-3-yl)-1H-imidazole

HRID 539458Notes

Reaction equation

HRID 539458 reaction equation
Cl[CH2:2][CH:3]=O.C([O-])(O)=O.[Na+].[CH:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([CH3:21])[CH3:20])[C:14]=1[NH:22][C:23]([C:25]1[CH:26]=[C:27]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:28]=[C:29]([O:31][CH3:32])[CH:30]=1)=[NH:24])([CH3:12])[CH3:11].C(N)(C)C>O.C(OCC)(=O)C>[CH:19]([C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH:10]([CH3:11])[CH3:12])[C:14]=1[N:22]1[CH:3]=[CH:2][N:24]=[C:23]1[C:25]1[CH:26]=[C:27]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:28]=[C:29]([O:31][CH3:32])[CH:30]=1)([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 33ChloroacetaldehydeHCID 6363IsopropylamineHCID 516892Sodium BicarbonateHCID 178492405HCID 178492405, compound

Product 1

HCID 706543721-(2,6-diisopropylphenyl)-2-(5-methoxy-[1,1'-biphenyl]-3-yl)-1H-imidazoleYield 98.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 250 mL round bottom flask was mixed 2-chloroacetaldehyde (5.36 g, 34.2 mmol), NaHCO3 (2.87 g, 34.2 mmol), N-(2,6-diisopropylphenyl)-5-methoxy-[1,1′-biphenyl]-3-carboximidamide (6.6 g, 17.08 mmol) were charged in a flask and 100 mL of iso-propyl amine was added. The reaction mixture was heated up to reflux for 3 hours. The reaction mixture was diluted with water and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate. After silica gel chromatography with 10% ethyl acetate in hexane as solvent, 6.9 g of product was obtained.

Workup

  1. additionwere charged in a flask
  2. temperatureThe reaction mixture was heated up
  3. temperatureto reflux for 3 hours
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate

Sources & evidence

ORD record
ord-20ef0aafc95e4b3d9de80b86ed59b5eb
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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