Sodium Hydroxide → 2-(Methylthio)-1H-imidazole-4,5-dimethanol

HRID 1728958Notes

Reaction equation

HRID 1728958 reaction equation
C[N:2]1[C:6]([C:7](OCC)=[O:8])=[C:5]([C:12](OCC)=[O:13])[N:4]=[C:3]1[S:17][CH3:18].[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].[OH-].[Na+]>CCOCC.O.ClCCl>[CH3:18][S:17][C:3]1[NH:4][C:5]([CH2:12][OH:13])=[C:6]([CH2:7][OH:8])[N:2]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 166653HydrideHCID 303834Diethyl 1-methyl-2-(methylthio)-1H-imidazole-4,5-dicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 537323532-(Methylthio)-1H-imidazole-4,5-dimethanol

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the above diethyl 2- (methylthio)-4,5-imidazoledicarboxylate (23 mmol) in freshly distilled anhydrous dichloromethane (50 mL) is added slowly to a stirred suspension of lithium aluminum hydride (69 mmol) in anhydrous ether (140 mL) at 0°-5° C. The mixture is stirred at about 0°-5° C. for about 3 hours after the addition is completed, then for about 1 hour at room temperature. The excess hydride is carefully decomposed by the slow, sequential addition of water (2.6 mL), 15% sodium hydroxide solution (2.6 mL), and water (7.8 mL). The precipitate of inorganic salts is filtered and extracted continuously for about 24 hours with tetrahydrofuran heated under reflux in a Soxhlet apparatus. The tetrahydrofuran solution is combined with the filtrate from the reaction mixture and concentrated to dryness in vacuo. The product is dried in vacuo and crystallized from tetrahydrofuran to give 2-(methylthio)-4,5-bis(hydroxymethyl) imidazole.

Workup

  1. additionafter the addition
  2. waitfor about 1 hour at room temperature
  3. filtrationThe precipitate of inorganic salts is filtered
  4. extractionextracted continuously for about 24 hours with tetrahydrofuran
  5. temperatureheated
  6. temperatureunder reflux in a Soxhlet apparatus
  7. concentrationconcentrated to dryness in vacuo
  8. customThe product is dried in vacuo
  9. customcrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-fa3a6b6d18c84010ae48546a71474d5d
Source dataset
uspto-grants-1994_07
Patent number
US05329012

Reaction notes

Loading…