Sodium Bicarbonate → HCID 66612217, compound

HRID 2390475Notes

Reaction equation

HRID 2390475 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-446ed2824ec54cc3bd3a2c2e743732b4
Source dataset
uspto-grants-2012_09
Patent number
US08273764B2

Reaction notes

Loading…