Sulfuryl chloride → 2-Chloro-5-methoxybenzothiazole

HRID 1487713Notes

Reaction equation

HRID 1487713 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[S:15][C:14](S)=[N:13][C:12]=2[CH:17]=1>C1COCC1.CCOC(C)=O>[Cl:4][C:14]1[S:15][C:11]2[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:17][C:12]=2[N:13]=1

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 178488276HCID 178488276, compound

Product 1

HCID 70592002-Chloro-5-methoxybenzothiazoleYield 20%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sulfuryl chloride (1.64 mL) was added to a solution of 5-methoxy-2-mercaptobenzothiazole in THF (20 mL). After stirring overnight, ice water was added. The reaction mixture was allowed to warm to rt and was diluted with EtOAc (100 mL). This was washed with water (50 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The material was purified by column chromatography (0 to 3% EtOAc in hexanes gradient), yielding 0.407 g (20%) of the title compound as a white solid. LC-MS: RT=9.05 min., [M+H]+=200.0. Rf=0.38 in 10% EtOAc/Hexanes.

Workup

  1. washThis was washed with water (50 mL) and brine (50 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe material was purified by column chromatography (0 to 3% EtOAc in hexanes gradient)

Sources & evidence

ORD record
ord-a3edce1aeb9346c89d681cab1a1e4803
Source dataset
uspto-grants-2016_08
Patent number
US09428522B2

Reaction notes

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