Sodium Hydroxide → HCID 23685598, compound
Reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][SH:12])=[CH:9][C:4]=2[O:3][CH2:2]1.Br[CH2:14][CH2:15][S:16]([O-:19])(=[O:18])=[O:17].[Na+:20].[OH-].[Na+]>C(O)C.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][S:12][CH2:14][CH2:15][S:16]([O-:19])(=[O:18])=[O:17])=[CH:9][C:4]=2[O:3][CH2:2]1.[Na+:20]Participants
Procedure
15 g of 2-(1,3-benzodioxol-5-yl)ethanethiol and 17.4 g of sodium 2-bromoethanesulfonate were dissolved in a mixture of 280 ml of ethanol and 120 ml of water. 3.3 g of sodium hydroxide was added to the solution and the mixture was heated under reflux for 1 h. The reaction mixture was concentrated and 500 ml of ethyl acetate and 500 ml of water were added thereto. After separation of the layers, the aqueous layer was acidified with hydrochloric acid. After extraction with n-butanol, the extract was washed with a saturated aqueous common salt solution. The solvent was distilled off to obtain 19 g of a faint yellow residue. This product was dissolved in a solution of 2.94 g of sodium hydroxide in dilute methanol and recrystallized therefrom to obtain 14.7 g of the intended compound in the form of colorless crystals.
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 1 h
- concentrationThe reaction mixture was concentrated
- addition500 ml of ethyl acetate and 500 ml of water were added
- customAfter separation of the layers
- extractionAfter extraction with n-butanol
- washthe extract was washed with a saturated aqueous common salt solution
- distillationThe solvent was distilled off
Sources & evidence
- ORD record
- ord-bcef9a4a4cee418d8c02d9b304f7598d
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05110956
Reaction notes
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