Thionyl Chloride → 2H-1,4-Benzothiazin-3(4H)-one, 2-(2-chloroethyl)-4-methyl-

HRID 235647Notes

Reaction equation

HRID 235647 reaction equation
O[CH2:2][CH2:3][CH:4]1[C:9](=[O:10])[N:8]([CH3:11])[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[S:5]1.S(Cl)([Cl:18])=O>ClCCl>[Cl:18][CH2:2][CH2:3][CH:4]1[C:9](=[O:10])[N:8]([CH3:11])[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[S:5]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20220115HCID 20220115, compound

Product 1

HCID 202201062H-1,4-Benzothiazin-3(4H)-one, 2-(2-chloroethyl)-4-methyl-Yield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.90 g of 2-(2-hydroxyethyl)-4-methyl-2H-1,4-benzothiazin-3(4H)-one in 20 ml of dichloromethane, was added dropwise 5 ml of thionyl chloride with stirring at room temperature. The mixture was stirred for one hour and then concentrated. The concentrate was subjected to a column chromatography on silica-gel (35 g). From the eluate with hexane-ethyl acetate (4:1, v/v) was obtained 5.05 g (95.3%) of 2-(2-chloroethyl)-4-methyl-2H-1,4-benzothiazin-3(4H)-one as an oily substance.

Workup

  1. stirringThe mixture was stirred for one hour
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4c29d4c3d8fa42169c7113f2e728fc9d
Source dataset
uspto-grants-1987_02
Patent number
US04640916

Reaction notes

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