Sodium Hydroxide → HCID 23172629, compound

HRID 1728963Notes

Reaction equation

HRID 1728963 reaction equation
[CH2:1]([N:4]1[C:8]([C:9](OCC)=[O:10])=[C:7]([C:14](OCC)=[O:15])[N:6]=[C:5]1[S:19][CH3:20])[CH2:2][CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].[OH-].[Na+]>ClCCl.CCOCC.O>[CH2:1]([N:4]1[C:8]([CH2:9][OH:10])=[C:7]([CH2:14][OH:15])[N:6]=[C:5]1[S:19][CH3:20])[CH2:2][CH3:3]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 54489461HCID 54489461, compound

Product 1

HCID 23172629HCID 23172629, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the above-identified diethyl 1-n-propyl-2-(methylthio)imidazole-4,5-dicarboxylate (23 mmol) in anhydrous dichloromethane (50 mL) was slowly (1 hour) added to a stirred suspension of lithium aluminum hydride (69 mmol) in anhydrous ether (140 mL) at 0.5° C. under nitrogen. The mixture was stirred at 0°-5° C. for 3 hours after the addition was completed, then at ambient temperature for 1 hour. The excess hydride was 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 was filtered and extracted continuously for 24 hours with tetrahydrofuran heated under reflux in a Soxhlet apparatus. The tetrahydrofuran solution was combined with the filtrate from the reaction mixture and reduced to dryness in vacuo. The solid residue was crystallized from acetone and identified as 1-n-propyl-2-(methylthio)-4,5-bis(hydroxymethyl)imidazole (48% yield).

Workup

  1. custom(1 hour)
  2. additionafter the addition
  3. waitat ambient temperature for 1 hour
  4. filtrationThe precipitate of inorganic salts was filtered
  5. extractionextracted continuously for 24 hours with tetrahydrofuran
  6. temperatureheated
  7. temperatureunder reflux in a Soxhlet apparatus
  8. customThe solid residue was crystallized from acetone

Sources & evidence

ORD record
ord-aa6453286ba048a38da94efcf202eaba
Source dataset
uspto-grants-1994_07
Patent number
US05329012

Reaction notes

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