Imidazole → HCID 20564366, compound

HRID 848752Notes

Reaction equation

HRID 848752 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH:8]([N:11]([CH:23]([CH3:25])[CH3:24])[C:12](=[O:22])[CH:13](Cl)[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)([CH3:10])[CH3:9]>CN(C)C=O>[CH:23]([N:11]([CH:8]([CH3:10])[CH3:9])[C:12](=[O:22])[CH:13]([C:14]1[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=1)[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 20564369HCID 20564369, compound

Product 1

HCID 20564366HCID 20564366, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

While stirring, a solution of 4.5 g of imidazole in 30 ml of dimethylformamide is dripped into a suspension of 1.3 g of sodium hydride in 30 ml of dimethylformamide. When no more gas evolves, a solution of 13.6 g of α-chloro-α-(4-chlorophenyl)-acetic acid-diisopropyl amide (see d)) in 100 ml of dimethylformamide is dripped in and the mixture is stirred overnight at room temperature. The oil which remains after the solvent has been evaporated off is taken up in 100 ml of dichloromethane and shaken 5 times, each time with 100 ml of 5% strength sodium chloride solution. The organic phase is then concentrated and chromatographed on silica gel (25×6 cm) using dichloromethane/acetone (9:1). After 2 l of first runnings have been separated off, the product fractions are obtained from which, after concentration and trituration with 10 ml of diisopropyl ether, 8.9 g of colorless crystals (m.p.: 112° C.) are isolated.

Workup

  1. stirringis stirred overnight at room temperature
  2. customhas been evaporated off
  3. stirringshaken 5 times
  4. concentrationThe organic phase is then concentrated
  5. customchromatographed on silica gel (25×6 cm)
  6. customAfter 2 l of first runnings have been separated off
  7. customthe product fractions are obtained from which
  8. concentrationafter concentration and trituration with 10 ml of diisopropyl ether, 8.9 g of colorless crystals (m.p.: 112° C.)
  9. customare isolated

Sources & evidence

ORD record
ord-08e6e8fed4a840a288729760acdb99f1
Source dataset
uspto-grants-1981_10
Patent number
US04297364

Reaction notes

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