Sulfuryl chloride → 4-Chloro-2,3-dihydro-1,2-benzothiazol-3-one

HRID 502608Notes

Reaction equation

HRID 502608 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([S:11]C)[C:3]=1/[CH:4]=[N:5]/O.S(Cl)(Cl)(=O)=[O:14]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]2[C:4](=[O:14])[NH:5][S:11][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 17910216(NE)-N-[(2-chloro-6-methylsulfanylphenyl)methylidene]hydroxylamine

Product 1

HCID 574365604-Chloro-2,3-dihydro-1,2-benzothiazol-3-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

(E)-2-Chloro-6-(methylthio)benzaldehyde oxime (12.37 g) was dissolved in toluene (35 mL). Sulfuryl chloride (5.4 ml, 66.24 mmol) was added, dropwise to the solution at 0° C., followed by heating at 80° C. for 1 h. After the completion of the reaction, the reaction mixture was cooled to room temperature and a white precipitate formed. The solid was collected by vacuum filtration, washed with toluene and air dried to 4-chlorobenzo[d]isothiazol-3(2H)-one (6 g). (This method is general for other 2-(methythio) benzaldehyde oximes.) 1H NMR (300 MHz, DMSO-d6): 7.90 (t, 1H), 7.55 (t, 1H), 7.41 ppm (d, 1H). MW=186 confirmed by LC-MS, tr=2.38 min (Method B) MH+=187.

Workup

  1. customAfter the completion of the reaction
  2. temperaturethe reaction mixture was cooled to room temperature
  3. customa white precipitate formed
  4. filtrationThe solid was collected by vacuum filtration
  5. washwashed with toluene and air
  6. dry with materialdried to 4-chlorobenzo[d]isothiazol-3(2H)-one (6 g)
  7. customconfirmed by LC-MS, tr=2.38 min (Method B) MH+=187

Sources & evidence

ORD record
ord-dfacf1a4ce5644e48c25069af136a072
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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