HCID 19811320, compound → HCID 19811367, compound

HRID 373074Notes

Reaction equation

HRID 373074 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14](OC)=[O:15])=[CH:13][C:8]=2[NH:7][C:6]1=[O:18].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH2:14][OH:15])=[CH:13][C:8]=2[NH:7][C:6]1=[O:18]

Participants

4

Reactant 2

HCID 19811320HCID 19811320, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19811367HCID 19811367, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.37 g of 1,3-dihydro-1-(2dimethylaminoethyl)-5-methoxycarbonyl-2H-benzimidazol-2-one in 15 ml of tetrahydrofuran was added 0.10 g of lithium aluminum hydride. After being stirred for 1 hour at room temperature, the reaction was quenched by the addition of 3.0 g of sodium sulfate hydrate. The solid was removed by filtration and the solvent was evaporated in vacuo. The residue was chromatographed on silica gel using chloroform-methanol-ammonium hydroxide (40:10:1) to provide 0.20 g of 1,3-dihydro-1-(2-dimethylaminoethyl)-5-hydroxymethyl-2H-benzimidazol-2-one

Workup

  1. customthe reaction was quenched by the addition of 3.0 g of sodium sulfate hydrate
  2. customThe solid was removed by filtration
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-71823789066848f19e1f87d532d88fec
Source dataset
uspto-grants-1992_11
Patent number
US05162318

Reaction notes

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