Dimethylformamide → HCID 178488774, compound

HRID 457385Notes

Reaction equation

HRID 457385 reaction equation
Cl.[C:2]([NH2:10])(=N)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:11](=[O:14])([O-])[O-].[K+].[K+].C[N:18]([CH:20]=O)[CH3:19]>>[C:3]1([C:19]2[NH:18][CH:20]=[C:2]([C:3]3[CH:4]=[CH:5][C:6]([O:14][CH3:11])=[CH:7][CH:8]=3)[N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 80289Benzamidine, hydrochloride

Product 1

HCID 178488774HCID 178488774, compound

Conditions

Temperature
60 °C

Procedure

To a solution of benzamidine hydrochloride (31.22 g, 0.2 mmol, 1.17 eq.) in 250 ml of DMF is added potassium carbonate (69 g, 0.5 mol). 2-bromo-4′-methoxyacetophnone is dissolved in 200 ml of DMF and added to the reaction flask dropwise at 55° C. After the addition, the reaction mixture is stirred at 60° C. for 3 h, then cooled to room temperature and poured into 1000 ml of ice-water, the mixture is extracted with ethyl acetate (150 ml×4), washed with water and brine, dried over sodium sulfate, purified through flash chromatography to give 30 g of 2-phenyl-4-(4-methoxyphenyl)imidazole. 1H NMR (400 MHz, CDCl3) δ 7.86 (2H, d, J=6.8 Hz), 7.43˜7.25 (5H, m), 6.93(2H, d, J=8.8 Hz), 3.83 (3H, s); MS (+VE) m/z 251 (M+1).

Workup

  1. additionadded to the reaction flask dropwise at 55° C
  2. additionAfter the addition
  3. temperaturecooled to room temperature
  4. extractionthe mixture is extracted with ethyl acetate (150 ml×4)
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. custompurified through flash chromatography

Sources & evidence

ORD record
ord-47ae9dfc59864c9f9f4a59f7adaf6b81
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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