Sodium Bicarbonate → HCID 20824482, compound

HRID 585729Notes

Reaction equation

HRID 585729 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([OH:15])=[O:14])=[CH:12][C:7]=2[S:6][CH2:5][CH2:4][CH2:3]1.O1CCOC[CH2:17]1.Cl.C(=O)([O-])O.[Na+]>CO>[CH3:17][O:14][C:13]([C:11]1[CH:10]=[CH:9][C:8]2[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][S:6][C:7]=2[CH:12]=1)=[O:15]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 22337349HCID 22337349, compound

Product 1

HCID 20824482HCID 20824482, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This 5-oxo-2,3,4,5-tetrahydro-1-benzothiepine-8-carboxylic acid (3.42 g) was dissolved in methanol (100 ml) and 4N hydrochloric acid dioxane solution (15 ml) was added. The mixture was stirred under reflux for 3 hr. The reaction mixture was cooled to room temperature and saturated aqueous sodium hydrogencarbonate solution (250 ml) was added. The mixture was extracted with ethyl acetate. The obtained organic layer was washed with water, saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure to give the objective 5-oxo-2,3,4,5-tetrahydro-1-benzothiepine-8-carboxylic acid methyl ester (3.35 g) as colorless crystals.

Workup

  1. temperatureunder reflux for 3 hr
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with water, saturated aqueous sodium hydrogencarbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f1694191a2d44d07a6f0c6438447d789
Source dataset
uspto-grants-2005_08
Patent number
US06933305B2

Reaction notes

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