Sodium Hydroxide → HCID 14257103, compound

HRID 622110

Reaction equation

HRID 622110 reaction equation
[C:1]([C:6]1[N:10]([CH3:11])[C:9]([S:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[N:8][C:7]=1[CH3:22])(OCC)=[O:2].[H-].[Al+3].[H-].[H-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+]>CCOCC.O>[CH3:11][N:10]1[C:6]([CH2:1][OH:2])=[C:7]([CH3:22])[N:8]=[C:9]1[S:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 14257102HCID 14257102, compoundHCID 21226445Aluminium lithium hydrideHCID 21584524Aluminiumhydride2×

Product 1

HCID 14257103HCID 14257103, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent4×

Conditions

Temperature
0 °C

Procedure

5-Carbethoxy-1,4-dimethyl-2-(4-methoxybenzylthio)imidazole (31 g, 0.1 mole) dissolved in ether (250 ml) was added dropwise to a solution of aluminum hydride in ether stirred at 0° C. [the aluminum hydride in ether was prepared by adding lithium aluminum hydride (7.4 g, 0.19 mole) in portions to a solution of aluminum chloride (8.6 g, 0.065 mole) stirred in ether (200 ml) at 0° C⟧ The mixture was stirred at 0° C. for 1 hour, treated with water and 10% aqueous sodium hydroxide, filtered and concentrated in vacuo. The resulting oil was dissolved in methylene chloride, dried with magnesium sulfate, filtered and concentrated in vacuo to give 1,4-dimethyl-5-hydroxymethyl-2-(4-methoxybenzylthio)imidazole.

Workup

  1. customwas prepared
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resulting oil was dissolved in methylene chloride
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6a7dc7cd8ded4a3c9867fe85a2edfb94
Source dataset
uspto-grants-1988_09
Patent number
US04769386

Linked notes

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