Sodium sulfate decahydrate → 4-[2-Amino-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butan-1-ol

HRID 1628439Notes

Reaction equation

HRID 1628439 reaction equation
[N:1]([C:4]1[N:8]([CH2:9][CH2:10][CH2:11][C:12](OCC)=[O:13])[C:7]2[C:17]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][CH:19]=[C:20]([Cl:21])[C:6]=2[N:5]=1)=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[NH2:1][C:4]1[N:8]([CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[C:7]2[C:17]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][CH:19]=[C:20]([Cl:21])[C:6]=2[N:5]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 86632866Ethyl 4-[2-azido-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate

Product 1

HCID 687615864-[2-Amino-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butan-1-olYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-[2-azido-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate (190 mg, 0.500 mmol) in tetrahydrofuran (3.0 mL) was added lithium aluminum hydride (57 mg, 1.5 mmol) portionwise at 0° C. After stirring for 1 hr, sodium sulfate decahydrate (300 mg) was added to the mixture, which was stirred for 1 hr. Insoluble materials were filtered off and the filtrate was concentrated in vacuo to give the title compound (135 mg, 0.435 mmol, 87%) as a colorless solid.

Workup

  1. stirringwas stirred for 1 hr
  2. filtrationInsoluble materials were filtered off
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6bf0e941d0cd42b3853fcc22482221c0
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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