Potassium Carbonate → HCID 66146991, compound

HRID 1186372Notes

Reaction equation

HRID 1186372 reaction equation
[NH:1]1[C:5]([CH:6]=[O:7])=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][CH:16]1[CH2:18][CH2:17]1>CN(C)C=O>[CH:16]1([CH2:15][N:1]2[C:5]([CH:6]=[O:7])=[CH:4][N:3]=[CH:2]2)[CH2:18][CH2:17]1.[CH:16]1([CH2:15][N:3]2[CH:4]=[C:5]([CH:6]=[O:7])[N:1]=[CH:2]2)[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 764281H-Imidazole-4-carbaldehydeHCID 81503Bromomethylcyclopropane

Product 2

HCID 66146991HCID 66146991, compoundYield 34%HCID 86657935HCID 86657935, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to Step 1 of Reference Example 8-47, by use of 1H-imidazole-5-carbaldehyde (400 mg, 4.16 mmol) dissolved in N,N-dimethylformamide (6 mL), potassium carbonate (1.15 g, 8.32 mmol) and (bromomethyl)cyclopropane (0.444 mL, 4.58 mmol), the mixture was stirred and reacted at room temperature for 2 hours. Then, purification by preparative thin-layer chromatography (chloroform/methanol=30/1, 50/1) was performed to give 1-(cyclopropylmethyl)-1H-imidazole-5-carbaldehyde (212 mg, yield: 34%) and 1-(cyclopropylmethyl)-1H-imidazole-4-carbaldehyde (209 mg, yield: 33%). 1-(cyclopropylmethyl)-1H-imidazole-5-carbaldehyde

Workup

  1. customreacted at room temperature for 2 hours
  2. customThen, purification by preparative thin-layer chromatography (chloroform/methanol=30/1, 50/1)

Sources & evidence

ORD record
ord-5fd6a77b3baa4aec924a6126e3d7f5c3
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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