Hydrochloric Acid → HCID 19596418, compound

HRID 612800Notes

Reaction equation

HRID 612800 reaction equation
C[O:2][C:3]([C:5]1[NH:9][C:8]([CH2:10][CH2:11][CH2:12][CH3:13])=[N:7][C:6]=1[C:14]([O:16]C)=[O:15])=[O:4].[I:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1.[H-].[Na+].Cl>CN(C=O)C.CO>[CH2:10]([C:8]1[N:7]([CH2:23][C:22]2[CH:25]=[CH:26][C:19]([I:18])=[CH:20][CH:21]=2)[C:6]([C:14]([OH:16])=[O:15])=[C:5]([C:3]([OH:2])=[O:4])[N:9]=1)[CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2×HCID 9542584-Iodobenzyl bromideHCID 14955796Dimethyl 2-butyl-1H-imidazole-4,5-dicarboxylate

Product 1

HCID 19596418HCID 19596418, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Dimethyl 2-butylimidazol-4,5-dicarboxylic acid (7.12 g, 29.6 mmol) and 4-iodobenzyl bromide (10.56 g, 35.5 mmol) were dissolved in DMF (50 ml), and 60% oily sodium hydride (1.3 g, 32.5 mmol) was added in small portions while stirring at room temperature. The reaction solution was stirred at room temperature for 2 hours and methanol was added to treat excess sodium hydride. Then the reaction solution was neutralized with 2N HCl and the product was extracted with dichloromethane. The extracted solution was dried over sodium sulfate and concentrated in reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to give the titled compound (11.1 g, 82%) as a tan solid (mp:98-99° C., Rf:0.60 silica gel-ethyl acetate/hexane/=1/1). This has the following NMR spectrum.

Workup

  1. stirringThe reaction solution was stirred at room temperature for 2 hours
  2. extractionthe product was extracted with dichloromethane
  3. dry with materialThe extracted solution was dried over sodium sulfate
  4. concentrationconcentrated in reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-cdf31f20f8224348856ae100cc0069cf
Source dataset
uspto-grants-1999_12
Patent number
US06005105

Reaction notes

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