Sulfuryl chloride → 2,5-Dichloro-1,3-benzothiazole

HRID 70135Notes

Reaction equation

HRID 70135 reaction equation
S(Cl)([Cl:4])(=O)=O.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[S:14][C:13](S)=[N:12][C:11]=2[CH:16]=1>>[Cl:4][C:13]1[S:14][C:10]2[CH:9]=[CH:8][C:7]([Cl:6])=[CH:16][C:11]=2[N:12]=1

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 178527796HCID 178527796, compound

Product 1

HCID 133148162,5-Dichloro-1,3-benzothiazole

Procedure

Sulfuryl chloride (10 mL) was added to 5-chloro-2-mercaptobenzothiazole at 0° C. After complete addition, the reaction mixture was allowed to warm to rt. After 2 h, the reaction mixture was poured into ice water (100 mL). This was allowed to warm to rt and was extracted with EtOAc (3×). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. The material was used without further purification. LC-MS: RT=10.03 min., compound does not ionize.

Workup

  1. additionAfter complete addition
  2. temperatureto warm to rt
  3. extractionwas extracted with EtOAc (3×)
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe material was used without further purification

Sources & evidence

ORD record
ord-956387bfdf0649ccac9a790221dc29fc
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

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