Acetone → HCID 22596709, compound

HRID 2296720Notes

Reaction equation

HRID 2296720 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]=[C:7]([NH:10][C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:8]([CH3:9])[C:4]=2[C:3]=1[C:21]([NH2:23])=[O:22].[C:24]1(C)[CH:29]=CC(S(O)(=O)=O)=C[CH:25]=1.CC(C)=O.C(=O)(O)[O-].[Na+]>CCOC(C)=O>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[NH:10][C:7]1[N:8]([CH3:9])[C:4]2=[C:3]3[C:2](=[CH:20][CH:19]=[C:5]2[N:6]=1)[NH:1][C:24]([CH3:29])([CH3:25])[NH:23][C:21]3=[O:22]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 113939665-Amino-2-(2,6-dichlorophenylamino)-3-methyl-3H-benzoimidazole-4-carboxylic acid amide

Product 1

HCID 22596709HCID 22596709, compoundYield 333.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 38 mg (0.11 mmol) of 5-amino-2-(2,6-dichlorophenylamino)-3-methyl-3H-benzimidazole-4-carboxylic acid amide (Example 7), 3 mg (0.02 mmol) p-toluenesulfonic acid, and 2 mL (27 mmol) of acetone was stirred at room temperature for 1 h, then heated to reflux for 1.5 h. The reaction was cooled and poured into a mixture of saturated aqueous sodium bicarbonate and EtOAc. The aqueous phase was extracted with EtOAc, the combined organics were extracted with saturated aqueous sodium bicarbonate, brine, dried (MgSO4), treated with activated carbon, filtered, and concentrated in vacuo to afford 26 mg of an orange solid. The crude product was chromatographed over silica gel to afford 20 mg (47%) of title compound 17, mp 238-239° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.5 h
  3. temperatureThe reaction was cooled
  4. extractionThe aqueous phase was extracted with EtOAc
  5. extractionthe combined organics were extracted with saturated aqueous sodium bicarbonate, brine
  6. dry with materialdried (MgSO4)
  7. additiontreated with activated carbon
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b74d48e7e8b94d988f4bdcbd19f79b5d
Source dataset
uspto-grants-2002_12
Patent number
US06489328B2

Reaction notes

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