Hydrochloric Acid → HCID 22387955, compound

HRID 1699825Notes

Reaction equation

HRID 1699825 reaction equation
[CH3:1][C:2]1[N:3](COCC[Si](C)(C)C)[C:4]2[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:7][C:5]=2[N:6]=1.Cl.C(=O)([O-])O.[Na+].C(OCC)(=O)C>C(O)C>[CH3:1][C:2]1[NH:3][C:4]2[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:7][C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 22387741Ethyl 2-methyl-1-(2-(trimethylsilyl)ethoxymethyl)-1H-thieno[2,3-d]imidazol-5-carboxlate

Product 1

HCID 22387955HCID 22387955, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-methyl-1-(2-(trimethylsilyl)ethoxymethyl)-1H-thieno[2,3-d]imidazol-5-carboxlate (745 mg) was dissolved in ethanol (10 ml) and 6N hydrochloric acid (10 ml) was added, which was followed by reflux under heating for 1 hr. A saturated aqueous sodium hydrogencarbonate solution was added under ice-cooling until the solution became weak alkaline, and the mixture was stirred with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the objective compound (370 mg) as white crystals.

Workup

  1. temperatureby reflux
  2. temperatureunder heating for 1 hr
  3. temperaturecooling until the solution
  4. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-652cdab4d1c24ed2b8f59b75ca04dccd
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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