Potassium Carbonate → HCID 21891611, compound

HRID 987458Notes

Reaction equation

HRID 987458 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:14]([CH3:15])[C:13]2[CH:16]=[C:17]([O:24][CH3:25])[C:18]([O:22][CH3:23])=[C:19]([O:20][CH3:21])[C:12]=2[N:11]=1)(C(C)(C)C)(C)C.[Si](OCC1N(C)C2C(OC)=C(OC)C(OC)=CC=2N=1)(C(C)(C)C)(C)C.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O.C1COCC1.[Cl-].[Na+].O>[OH:8][CH2:9][C:10]1[N:14]([CH3:15])[C:13]2[CH:16]=[C:17]([O:24][CH3:25])[C:18]([O:22][CH3:23])=[C:19]([O:20][CH3:21])[C:12]=2[N:11]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 21891603HCID 21891603, compoundHCID 21891643HCID 21891643, compound

Product 1

HCID 21891611HCID 21891611, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture (471 mg) of 2-tert-butyldimethylsilyloxymethyl-1-methyl-4,5,6-trimethoxybenzimidazole and 2-tert-butyldimethylsilyloxymethyl-1-methyl-5,6,7-trimethoxybenzimidazole was dissolved in a mixed solvent of acetic acid (5 mL), water (2.5 mL) and THF (2.5 mL), and the solution was stirred at 90° C. for 2 hours. Saturated brine was added to the reaction mixture, and the mixture was alkalified with an aqueous solution of potassium carbonate and then extracted with ethyl acetate. The resultant organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by preparative TLC on silica gel (chloroform:methanol=13:1) to obtain a mixture of the title compounds.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe resultant organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative TLC on silica gel (chloroform:methanol=13:1)
  6. customto obtain

Sources & evidence

ORD record
ord-90b4b72c9410446898aec5c2b2cf0c9e
Source dataset
uspto-grants-2003_10
Patent number
US06632810B2

Reaction notes

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