Sodium sulfate decahydrate → 2-[1-(2,4-Dichlorophenyl)-5-(diethylamino)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-2-yl]ethanol

HRID 1399015Notes

Reaction equation

HRID 1399015 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[N:15]1[C:19]2=[N:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[C:22]=3[N:18]2[CH2:17][CH:16]1[CH2:32][C:33](OC)=[O:34].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[N:15]1[C:19]2=[N:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[C:22]=3[N:18]2[CH2:17][CH:16]1[CH2:32][CH2:33][OH:34]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 57785854Methyl [1-(2,4-dichlorophenyl)-5-(diethylamino)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-2-yl]acetate

Product 1

HCID 577858692-[1-(2,4-Dichlorophenyl)-5-(diethylamino)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-2-yl]ethanolYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (20 mg, 0.54 mmol) in tetrahydrofuran (1.5 mL) was added a solution of methyl [1-(2,4-dichlorophenyl)-5-(diethylamino)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-2-yl]acetate (Example 72, 60.0 mg, 0.134 mmol) in tetrahydrofuran (1.5 mL) at 0° C. and the resultant mixture was stirred at 0° C. for 10 min. After sodium sulfate decahydrate (600 mg) was added at 0° C., the resultant mixture was filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 30-60% ethyl acetate/n-hexane gradient mixture to give the title compound as a solid (43.1 mg, 0.103 mmol, 77%). Analytically pure material was obtained by recrystallization from ethyl acetate/n-hexane.

Workup

  1. filtrationthe resultant mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel eluting with a 30-60% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-6860d1b5268446a18bafb4c609dbbd98
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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