Sulfuryl chloride → 2-Chloro-5-methoxybenzothiazole

HRID 549674Notes

Reaction equation

HRID 549674 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-91beeb4062ae4cfd9918dd3c2383bd7e
Source dataset
uspto-grants-2011_05
Patent number
US07943622B2

Reaction notes

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