Oxalyl chloride → 4-Chloro-2-(2-methoxyethyl)-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 729259Notes

Reaction equation

HRID 729259 reaction equation
[C:1]([Cl:6])(=O)[C:2](Cl)=[O:3].OC1C(=O)[N:10]([CH2:21][CH2:22][O:23][CH3:24])[S:11](=[O:20])(=[O:19])[C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[Cl:6][C:1]1[C:2](=[O:3])[N:10]([CH2:21][CH2:22][O:23][CH3:24])[S:11](=[O:19])(=[O:20])[C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 67243377HCID 67243377, compound

Product 1

HCID 672439094-Chloro-2-(2-methoxyethyl)-5-phenylisothiazol-3(2H)-one 1,1-dioxideYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.185 g, 1.46 mmol) was added dropwise to a solution of 4-hydroxy-2-(2-methoxyethyl)-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.250 g, 0.88 mmol) in DCM (15 mL). The mixture was refluxed for 2 days and then evaporated. The residue was dissolved in water and extracted 3 times with DCM. The combined organic layer was washed 2 times with water, dried through a phase separator and evaporated to give the title compound (0.245 g, 92%) as a solid; 1H NMR (500 MHz, CD3OD): δ 7.94-7.97 (m, 2H), 7.58-7.67 (m, 3H), 3.94 (t, 2H), 3.70 (t, 2H), 3.38 (s, 3H).

Workup

  1. temperatureThe mixture was refluxed for 2 days
  2. customevaporated
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted 3 times with DCM
  5. washThe combined organic layer was washed 2 times with water
  6. customdried through a phase separator
  7. customevaporated

Sources & evidence

ORD record
ord-154be78ff0c14f5688bf96dcaf17e60c
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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