Sodium borohydride → HCID 57572241, compound

HRID 2262743Notes

Reaction equation

HRID 2262743 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[C:9]([N:13]3[C:17]4[CH:18]=[CH:19][C:20]([C:22](=[O:24])[CH3:23])=[CH:21][C:16]=4[N:15]=[CH:14]3)[CH:10]=[CH:11][CH:12]=2)=[N:4][CH:3]=1.[BH4-].[Na+]>CO.O>[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[C:9]([N:13]3[C:17]4[CH:18]=[CH:19][C:20]([CH:22]([OH:24])[CH3:23])=[CH:21][C:16]=4[N:15]=[CH:14]3)[CH:10]=[CH:11][CH:12]=2)=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 67484095HCID 67484095, compound

Product 1

HCID 57572241HCID 57572241, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-{1-[3-(5-chloro-thiazol-2-yl)-phenyl]-1H-benzoimidazol-5-yl}-ethanone (6.3 g, 17.8 mmol) in methanol (75 ml) was added sodium borohydride (0.91 g, 23.9 mmol) and the resultant mixture was stirred at room temperature in a nitrogen atmosphere for 7 days. The reaction mixture was diluted with four volumes of water and extracted with ethyl acetate. The organic extract was washed with brine, dried over magnesium sulphate and evaporated in vacuo to leave the desired product (4.95 g, 78%). LC-ESI-HRMS of [M+H]+ shows 356.0635 Da. Calc. 356.062436 Da. dev. 3 ppm.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-94292abb39b14ba1a922eac5974e3ff0
Source dataset
uspto-grants-2010_12
Patent number
US07851490B2

Reaction notes

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