Chlorosuccinimide → N-(Methylsulfonyl)-2-(chloronitromethylene)-tetrahydro-2H-1,3-thiazine

HRID 1153718Notes

Reaction equation

HRID 1153718 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH2:8][S:7][C:6]1=[CH:11][N+:12]([O-:14])=[O:13])(=[O:4])=[O:3].[Cl:15]N1C(=O)CCC1=O>ClC(Cl)C>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH2:8][S:7][C:6]1=[C:11]([Cl:15])[N+:12]([O-:14])=[O:13])(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 544126983-(Methanesulfonyl)-2-(nitromethylidene)-1,3-thiazinane

Product 1

HCID 53757526N-(Methylsulfonyl)-2-(chloronitromethylene)-tetrahydro-2H-1,3-thiazine

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A stirred solution of 0.238 g of (1A), 0.15 g of N-chlorosuccinimide and about 1 mg of azoisobutyronitrile in 10 ml of dichloroethane was refluxed overnight. The resulting mixture was cooled, washed with water, dried (MgSO4) and stripped of solvent, giving a yellow oil. The oil was flash-chromatographed over silica gel, using methylene chloride as eluent, to give (2).

Workup

  1. temperatureThe resulting mixture was cooled
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customgiving a yellow oil
  5. customThe oil was flash-chromatographed over silica gel

Sources & evidence

ORD record
ord-c659ab3183964e4493d415ff33780810
Source dataset
uspto-grants-1984_12
Patent number
US04486427

Reaction notes

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