HCID 178477922, compound → 2,5-Dichloro-1,3-benzothiazole

HRID 1446867Notes

Reaction equation

HRID 1446867 reaction equation
ClC1C=CC2SC(S)=NC=2C=1.[Cl:12][C:13]1[S:14][C:15]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:16]=2[N:17]=1>S(Cl)(Cl)(=O)=O>[Cl:12][C:13]1[S:14][C:15]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:16]=2[N:17]=1

Participants

3

Reactant 1

HCID 178477922HCID 178477922, compound

Product 1

HCID 133148162,5-Dichloro-1,3-benzothiazoleYield 198.8%

Reagents, catalysts & solvents 1

HCID 24648Sulfuryl chlorideSolvent

Procedure

2,5-Dichlorobenzothiazole 5-Chloro-2-mercaptobenzothiazole (10.0 g) was added to sulfuryl chloride (50 ml) and the mixture was stirred at room temperature for a period of 1 hr. Excess sulfuryl chloride in the mixture was destroyed by the addition of water and the aqueous mixture was extracted with dichloromethane. The organic extract was washed with water, dried over anhydrous magnesium sulfate and passed through a short column of silica gel. The solvent was removed by distillation under reduced pressure to give 2,5-dichlorobenzothiazole (10.0 g) as pale yellow crystals, mp 70° C.

Workup

  1. customExcess sulfuryl chloride in the mixture was destroyed by the addition of water
  2. extractionthe aqueous mixture was extracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-a1ced0fe84a74a6f8e50aa5902b9f50d
Source dataset
uspto-grants-1982_02
Patent number
US04314065

Reaction notes

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