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

HRID 1153717Notes

Reaction equation

HRID 1153717 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH3:6][S:7]([N:10]1[CH2:15][CH2:14][CH2:13][S:12][C:11]1=[CH:16][N+:17]([O-:19])=[O:18])(=[O:9])=[O:8]>C(Cl)Cl>[CH3:6][S:7]([N:10]1[CH2:15][CH2:14][CH2:13][S:12][C:11]1=[C:16]([Cl:4])[N+:17]([O-:19])=[O:18])(=[O:8])=[O:9]

Participants

4

Reactant 2

HCID 24648Sulfuryl chloride2×HCID 544126983-(Methanesulfonyl)-2-(nitromethylidene)-1,3-thiazinane

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.25 g of redistilled sulfuryl chloride in 5 ml of methylene chloride was added drop-by-drop over a 5-minute period to a slurry of (1A) in 50 ml of methylene chloride in a nitrogen atmosphere at 0-5° C. The mixture was stirred for 30 minutes more, then allowed to warm to room temperature. Two drops more of sulfuryl chloride were added and the mixture was stirred for 5 minutes. The resulting mixture was washed with water, then with brine, dried (MgSO4), and stripped of solvent to give a yellow solid. The solid was triturated with ether to give (2), as a yellow solid, m.p. 149°-151° C. (with decomposition).

Workup

  1. stirringthe mixture was stirred for 5 minutes
  2. washThe resulting mixture was washed with water
  3. dry with materialwith brine, dried (MgSO4)
  4. customto give a yellow solid
  5. customThe solid was triturated with ether

Sources & evidence

ORD record
ord-e899d86d44a04276a33b9555012f37af
Source dataset
uspto-grants-1984_12
Patent number
US04486427

Reaction notes

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