Sodium Hydroxide → HCID 86691640, compound

HRID 2204025Notes

Reaction equation

HRID 2204025 reaction equation
[OH-].[Na+].[N:3]1([CH:8]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O-:17])=[O:16])[CH:7]=[CH:6][N:5]=[CH:4]1>CO.O>[N:3]1([CH:8]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86691641HCID 86691641, compound

Product 1

HCID 86691640HCID 86691640, compoundYield 125.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium hydroxide (0.67 g, 1.68 mmol) was added to a stirred solution of 8-(1H-imidazol-1-yl)octadecanoate (0.305 g, 0.84 mmol) in a mixture of methanol (9 ml) and water (3 ml) at 0° C., warmed to room temperature and stirring continued another 3 h. Methanol was removed from the mixture by evaporation. The pH was adjusted to 4 with 1N HCl, and the mixture extracted with dichloromethane (3×15 ml). 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, 83%).

Workup

  1. customMethanol was removed from the mixture by evaporation
  2. extractionthe mixture extracted 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-df5819331583414497eeb19bb269989d
Source dataset
uspto-grants-2016_06
Patent number
US09365597B2

Reaction notes

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