Sodium Bicarbonate → HCID 66612217, compound

HRID 1256601Notes

Reaction equation

HRID 1256601 reaction equation
[CH:1]([NH:5][C:6]1[C:7]([NH2:16])=[CH:8][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:11]=1)([CH2:3][CH3:4])[CH3:2].O[CH:18]([C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)S([O-])(=O)=O.[Na+].C(=O)([O-])O.[Na+]>CN(C=O)C>[CH:1]([N:5]1[C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:14])([F:15])[F:13])=[CH:8][C:7]=2[N:16]=[C:18]1[C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)([CH2:3][CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 23695668HCID 23695668, compoundHCID 43115315HCID 43115315, compound

Product 1

HCID 66612217HCID 66612217, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.76 g of N1-sec-butyl-4-trifluoromethylbenzene-1,2-diamine, 0.84 g of sodium hydroxy-pyridin-4-yl-methanesulfonate and 17 ml of DMF was stirred for 1 hour at 120° C. The reaction mixture was cooled down to room temperature. Into the reaction mixture was poured a saturated sodium hydrogen carbonate aqueous solution, and the mixture was extracted three times with ethyl acetate. The organic layer was dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, to obtain 0.91 g of 1-sec-butyl-2-pyridin-4-yl-5-trifluoromethyl-1H-benzimidazole (hereinafter, referred to as present active compound 201).

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cb9a3abe9e934b36a41f00cd530e334e
Source dataset
uspto-grants-2013_06
Patent number
US08461181B2

Reaction notes

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