Potassium Carbonate → HCID 19434458, compound

HRID 1735828Notes

Reaction equation

HRID 1735828 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[C:13]([O-])([O-])=O.[K+].[K+].BrC[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:28]([C:33]([O:35][CH3:36])=[O:34])=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:23][CH:22]=1>CN(C=O)C>[CH2:1]([C:5]1[N:6]([CH2:13][C:30]2[CH:31]=[CH:32][C:27]([C:24]3[CH:23]=[CH:22][CH:21]=[CH:26][CH:25]=3)=[C:28]([C:33]([O:35][CH3:36])=[O:34])[CH:29]=2)[C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 178418251HCID 178418251, compound

Product 1

HCID 19434458HCID 19434458, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 4.5 g of 2-butyl-4-chloro-5-formylimidazole and 6.75 g of K2CO3 in 200 ml of anhydrous DMF under nitrogen atmosphere is added under stirring with a solution of 8.1 g of methyl 4'-bromomethyl-1,1'-biphenyl-2-carboxylate in 10 ml of anhydrous DMF. The mixture is stirred at room temperature for 2 hours then concentrated under reduced pressure to 50 ml, poured into 500 ml of H2O and extracted with CH2Cl2. The organic phase is washed with H2O, dried over Na2SO4 and evaporated to dryness under reduced pressure. 9 of an orange oil are obtained which is used without further purification. 1H NMR (CDCl3), δ: 0.89 (t, 3 H); 1.45 (m, 2 H); 1.72 (m, 2 H); 2.66 (m, 2 H); 3.62 (s, 3 H); 5.59 (s, 2 H); 7.02-7.88 (m, 8 H); 9.76 (s, 1 H).

Workup

  1. additionis added
  2. concentrationthen concentrated under reduced pressure to 50 ml
  3. additionpoured into 500 ml of H2O
  4. extractionextracted with CH2Cl2
  5. washThe organic phase is washed with H2O
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness under reduced pressure
  8. custom9 of an orange oil are obtained which
  9. customis used without further purification

Sources & evidence

ORD record
ord-870af1547a9e4a009475a887277f1e80
Source dataset
uspto-grants-1996_07
Patent number
US05538987

Reaction notes

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