Diethyl Ether → 2-[Bromo(nitro)methylidene]-3-(methanesulfonyl)-1,3-thiazinane

HRID 1153716Notes

Reaction equation

HRID 1153716 reaction equation
[Br:1]Br.[CH3:3][S:4]([N:7]1[CH2:12][CH2:11][CH2:10][S:9][C:8]1=[CH:13][N+:14]([O-:16])=[O:15])(=[O:6])=[O:5].CCOCC>C(Cl)Cl>[CH3:3][S:4]([N:7]1[CH2:12][CH2:11][CH2:10][S:9][C:8]1=[C:13]([Br:1])[N+:14]([O-:16])=[O:15])(=[O:5])=[O:6]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24408BromineHCID 544126983-(Methanesulfonyl)-2-(nitromethylidene)-1,3-thiazinane

Product 1

HCID 541037362-[Bromo(nitro)methylidene]-3-(methanesulfonyl)-1,3-thiazinane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

A solution of 1.6 g of bromine in 10 ml of methylene chloride was added drop-by-drop over a period of 10 minutes to a solution of 2.38 g of (1A) in 50 ml of methylene chloride at 0° C. and under a nitrogen blanket. The resulting mixture was stirred for a further 10 minutes, charcoaled, and stripped of solvent. The residue was dissolved in a minimum amount of methylene chloride, then ether was added to the solution, resulting in a gum. The gum was dissolved in methylene chloride, the solution was charged onto a flash chromatograph column (silica gel) and the product was eluted with methylene chloride, to give (1) on workup.

Workup

  1. customresulting in a gum
  2. additionthe solution was charged onto a flash chromatograph column (silica gel)
  3. washthe product was eluted with methylene chloride

Sources & evidence

ORD record
ord-a82e981d620a46ba81833a55660a045c
Source dataset
uspto-grants-1984_12
Patent number
US04486427

Reaction notes

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