Ethyl Acetate → HCID 19815428, compound

HRID 653870Notes

Reaction equation

HRID 653870 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[NH:5][C:6]=1[CH2:7][OH:8].C([O-])([O-])=O.[K+].[K+].[N+:22]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1)([O-:24])=[O:23].CCOC(C)=O>CN(C=O)C.O>[Cl:1][C:2]1[N:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:5]([CH2:29][C:28]2[CH:31]=[CH:32][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=2)[C:6]=1[CH2:7][OH:8]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 19815317HCID 19815317, compound

Product 1

HCID 19815428HCID 19815428, compoundYield 118.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-2-heptyl-5-(hydroxymethyl)imidazole (5.2 g, 20.7 mmol) in dry DMF (100 mL) was added anhydrous K2CO3 (4.3 g, 31.1 mmol) followed by 4-nitrobenzylbromide (5.4 g, 24.9 mmol). The solution was stirred 3-5 hours at 65°-70°. The reaction mixture was poured into a separatory funnel containing EtOAc and H2O (300 mL each). The aqueous phase was extracted with EtOAc (150 mL) and the combined organic phases were washed three times with H2O (150 mL) before being dried (MgSO4), filtered and concentrated to give 9.0 g brown crude oil. Chromatography (silica gel, 450 g; 1:1 EtOAc/hexanes) gave 1.3 g (17% overall, 35% of theoretical); m.p. 110°-115°. NMR (200 MHz, CDCl3) δ 8.20 (d, 2H, 5Hz); 7.20 (d, 2H, 5Hz); 5.35 (s, 2H); 4.45 (s, 2H); 3.10-300 (m, 1H); 2.50 (t, 2H, 5Hz); 1.75-1.50 (m 2H); 1.40-1.10 (m, 8H); 0.90-0.75 (m, 3H). Mass spec. 365.

Workup

  1. additionThe reaction mixture was poured into a separatory funnel
  2. extractionThe aqueous phase was extracted with EtOAc (150 mL)
  3. washthe combined organic phases were washed three times with H2O (150 mL)
  4. dry with materialbefore being dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-99bd1966ac95490b8ef59f46797540f4
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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