Water → HCID 21276959, compound

HRID 2292141Notes

Reaction equation

HRID 2292141 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8](OCC)=O)[C:5]2[CH:13]=[C:14]([CH3:18])[C:15]([CH3:17])=[CH:16][C:4]=2[N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH2:25].[OH-].[Na+]>O1CCCC1>[CH3:1][C:2]1[N:6]([CH:7]([OH:25])[CH3:8])[C:5]2[CH:13]=[C:14]([CH3:18])[C:15]([CH3:17])=[CH:16][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21276952Ethyl 2-(2,5,6-trimethylbenzimidazol-1-yl)acetate

Product 1

HCID 21276959HCID 21276959, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 2-(2,5,6-trimethylbenzimidazol-1-yl)acetate (6.15 g) in dry tetrahydrofuran (20 ml) was added to a suspension of lithium aluminium hydride (0.95 g) was dry tetrahydrofuran (60 ml) at 0° C. The reaction was allowed to warm to room temperature and stirred at room temperature for 1 hour. Water (1 ml) was added dropwise to the reaction followed by 15% sodium hydroxide (3 ml) and water (3 ml). The suspension was filtered and the solvent removed under reduced pressure. The product was dissolved in dichloromethane, dried over magnesium sulphate and the solvent removed under reduced pressure. The residue was triturated with acetone, the solid filtered and dried under reduced pressure to yield the title compound (1.9 g, 37%), m.p. 191°-2° C. Found: C, 70.17; H, 8.07; N, 13.56. C12H16N2O requires: C, 70.59; H, 7.84; N, 13.72%.

Workup

  1. customat 0° C
  2. filtrationThe suspension was filtered
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe product was dissolved in dichloromethane
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent removed under reduced pressure
  7. customThe residue was triturated with acetone
  8. filtrationthe solid filtered
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-b2f1dec1082e48969d4a4f42904a5f6f
Source dataset
uspto-grants-1989_01
Patent number
US04801598

Reaction notes

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