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

HRID 258680Notes

Reaction equation

HRID 258680 reaction equation
[N+:1]([C:4](=[C:10]1[NH:15][CH2:14][CH2:13][CH2:12][S:11]1)C(OCC)=O)([O-:3])=[O:2].[OH-].[Na+]>C(O)(=O)C>[N+:1]([CH:4]=[C:10]1[NH:15][CH2:14][CH2:13][CH2:12][S:11]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71443329Ethyl nitro(1,3-thiazinan-2-ylidene)acetate

Product 1

HCID 428532-nitromethylenetetrahydro-2H-1,3-thiazine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.3 g of 1A 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 (1B) as a pale yellow solid, m.p. 76°-78°.

Workup

  1. additionThe addition
  2. extractionThe resulting mixture was extracted with methylene chloride
  3. dry with materialthe extract was dried (magnesium sulfate)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b524679e556d4e8b99190281e3c78b2e
Source dataset
uspto-grants-1977_07
Patent number
US04034091

Reaction notes

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