Sodium Hydroxide → 2-nitromethylenetetrahydro-2H-1,3-thiazine

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Reaction Steps

2.3 g of 5A was added to 10 ml of 20% aqueous sodium hydroxide and the mixture was stirred at room temperature for 12 hours. The resulting solution was treated dropwise with 3.5 g of acetic acid. The addition was accompanied by vigorous gas evolution. The resulting mixture was extracted with methylene chloride and the extract was dried (magnesium sulfate) and concentrated under reduced pressure to give tetrahydro-2-(nitromethylene)-2H-1,3-thiazine (5B) as a pale yellow solid, m.p.: 76°-78°.

Provenance & Evidence