Hydrochloric Acid → HCID 22387955, compound

HRID 1072803Notes

Reaction equation

HRID 1072803 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(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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 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-carboxylate (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 extracted 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. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f9c471b5798546acad49b24795f5fae5
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

Loading…