Sodium Hydroxide → HCID 86691639, compound

HRID 2204023Notes

Reaction equation

HRID 2204023 reaction equation
[OH-].[Na+].[N:3]1([CH:8]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]C)=[O:14])[CH:7]=[CH:6][N:5]=[CH:4]1>CO.O>[N:3]1([CH:8]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86691638HCID 86691638, compound

Product 1

HCID 86691639HCID 86691639, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium hydroxide (0.11 g, 2.75 mmol) was added to a stirred solution of methyl 6-(1H-imidazol-1-yl)octadecanoate (0.5 g, 1.37 mmol) in a mixture of methanol (9 ml) and water (3 ml) at 0° C., warmed to room temperature, and stirring continued for another 3 hours. Methanol was removed from the mixture by evaporation. The aqueous layer was acidified with 1N HCl up to pH 4, extracted with dichloromethane (3×15 ml), and the combined organic layers were washed with brine solution, dried on anhydrous MgSO4, and concentrated. Crude product was purified on silica gel column (5% methanol in dichloromethane) to obtain a gummy liquid (370 mg, 77%).

Workup

  1. customMethanol was removed from the mixture by evaporation
  2. extractionextracted with dichloromethane (3×15 ml)
  3. washthe combined organic layers were washed with brine solution
  4. dry with materialdried on anhydrous MgSO4
  5. concentrationconcentrated
  6. customCrude product was purified on silica gel column (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a6a2b4cab7d74acda1ce4b4658d3f2f4
Source dataset
uspto-grants-2016_06
Patent number
US09365597B2

Reaction notes

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