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

HRID 1926385Notes

Reaction equation

HRID 1926385 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](S)=[N:7][C:6]=2[CH:11]=1.S(Cl)([Cl:15])(=O)=O>>[Cl:15][C:8]1[S:9][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:11][C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 178527796HCID 178527796, compound

Product 1

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

Procedure

To 5-chloro-2-mercaptobenzothiazole (1.5 g, 7.4 mmol) was added sulfuryl chloride (5 mL, excess) with stirring below 5° C. under nitrogen. The resulting suspension was stirred for 3 h at rt, carefully poured onto ice (100 g), and stirred for another 2 h. The white solid that separated out was filtered off, washed repeatedly with cold water, and dried in vacuo to afford the title compound. 1H-NMR (CDCl3, 300 MHz): δ=7.95 (s, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.37 (d, J=8.7 Hz, 1H).

Workup

  1. stirringThe resulting suspension was stirred for 3 h at rt
  2. additioncarefully poured onto ice (100 g)
  3. stirringstirred for another 2 h
  4. customThe white solid that separated out
  5. filtrationwas filtered off
  6. washwashed repeatedly with cold water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-1df03bb5b26b4176875468810c62f7cc
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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