Imidazole → HCID 20508210, compound

HRID 549366Notes

Reaction equation

HRID 549366 reaction equation
Br[CH2:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1.[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1>CN(C)C=O.C(OCC)(=O)C>[Br:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3](=[O:13])[CH2:2][N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 795ImidazoleHCID 25143348HCID 25143348, compound

Product 1

HCID 20508210HCID 20508210, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-bromo-4-(4-bromophenyl)-2-butanone (0.5 mmol) and imidazole (102 mg, 1.5 mmol) in dry N,N-dimethylformamide (2 mL) was stirred at room temperature under a nitrogen atmosphere for 1 h. The mixture was then diluted with ethyl acetate (15 mL), and the solution was washed with water (4×15 mL). The separated organic phase was dried over anhydrous Na2SO4, and then the solvent was removed under reduced pressure to afford a residue that was chromatographed on a silica gel column using ethyl acetate as mobile phase to give 4-(4-bromophenyl)-1-(1H-imidazol-1-yl)-2-butanone as a white solid (111 mg, 76%): mp 79-80° C., Rf=0.50 (ethyl acetate-methanol 4:1 v/v); 1H NMR (400 MHz, CDCl3): δ 2.70 (t, J=7.2 Hz, 2H), 2.83 (t, J=7.2 Hz, 2H), 4.65 (s, 2H), 6.81 (bs, 1H), 7.02 (d, J=7.6 Hz, 2H), 7.09 (s, 1H), 7.37-7.40 (m, 3H); 13C NMR (100 MHz, CDCl3): δ 28.6, 40.9, 55.7, 120.1, 120.4, 130.0, 131.8, 138.0, 139.1, 202.3; HRMS (EI) Calcd. for C13H13BrN2O: 292.0211 (M+). Found: 292.0219.

Workup

  1. washthe solution was washed with water (4×15 mL)
  2. dry with materialThe separated organic phase was dried over anhydrous Na2SO4
  3. customthe solvent was removed under reduced pressure
  4. customto afford a residue that
  5. customwas chromatographed on a silica gel column

Sources & evidence

ORD record
ord-8ea9b6d2b3ac4fb2b19e42e50d278f8e
Source dataset
uspto-grants-2011_05
Patent number
US07943650B2

Reaction notes

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