Hydrochloric Acid → HCID 68600500, compound

HRID 1799698Notes

Reaction equation

HRID 1799698 reaction equation
[Si]([O:8][CH2:9][C:10]1[S:14][CH:13]=[N:12][C:11]=1/[CH:15]=[CH:16]\[S:17][C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(C(C)(C)C)(C)C.Cl.O.C(=O)(O)[O-].[Na+]>C1COCC1.[Cl-].[Na+].O>[OH:8][CH2:9][C:10]1[S:14][CH:13]=[N:12][C:11]=1/[CH:15]=[CH:16]\[S:17][C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 68602772HCID 68602772, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 68600500HCID 68600500, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

5-t-Butyldimethylsilyloxymethyl-4-((Z)-2-tritylthioethen-1-yl)thiazole (392 mg) was dissolved in 10 ml of THF, 0.7 ml of 5 N-aqueous hydrochloric acid was added to the solution, and the mixture was stirred at room temperature for 2 hr. Brine was added to the reaction solution, and the mixture was adjusted to pH 8 by the addition of sodium bicarbonate water. The mixture was extracted twice with ethyl acetate, followed by washing with brine. The organic layer was dried over anhydrous magnesium sulfate, was filtered, and was concentrated under the reduced pressure. Ethyl acetate (5 ml) and 5 ml of hexane were added to the residue, and the resultant solid was collected by filtration to give 180 mg of the title compound.

Workup

  1. extractionThe mixture was extracted twice with ethyl acetate
  2. washby washing with brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationwas filtered
  5. concentrationwas concentrated under the reduced pressure
  6. additionEthyl acetate (5 ml) and 5 ml of hexane were added to the residue
  7. filtrationthe resultant solid was collected by filtration

Sources & evidence

ORD record
ord-debbb97d41c24b62a532a56af3d03b79
Source dataset
uspto-grants-2013_01
Patent number
US08344154B2

Reaction notes

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