Sulfuryl chloride → HCID 19425177, compound

HRID 742185Notes

Reaction equation

HRID 742185 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7][N:8]1[C:12](=[O:13])[CH:11]=[CH:10][S:9]1)=[O:4].S(Cl)([Cl:17])(=O)=O>>[Cl:17][C:10]1[S:9][N:8]([CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[C:12](=[O:13])[CH:11]=1

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 19425176HCID 19425176, compound

Product 1

HCID 19425177HCID 19425177, compound

Conditions

Temperature
0 °C

Procedure

To prepare 2-(3-methoxycarbonylpropyl)-3-isothiazolone, Compound I (1.02 g, 2.5 mmol) was dissolved in25 ml distilled ethyl acetate and cooled to 0° C. Sulfuryl chloride (1.04 g, 7.75 mmol) was added slowly dropwise and the yellow solution stirred at 0° C. for 1 hr. During this time a white precipitate formed (5-chloro-2-(3-methoxycarbonylpropyl)-3-isothiazolone (200 mg)) which was removed by filtration. The resulting filtrate was concentrated and the residue flash-chromatographed (10% acetone-chloroform) to yield 2-(3-methoxycarbonylpropyl)-3-isothiazolone (120 mg) as a clear oil.

Workup

  1. dissolutionwas dissolved
  2. distillationin25 ml distilled ethyl acetate

Sources & evidence

ORD record
ord-57b0aea475bf43ed830e55ee7c9d9b08
Source dataset
uspto-grants-1996_09
Patent number
US05554542

Reaction notes

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