Water → Methyl benzo[c]isothiazole-4-carboxylate

HRID 1639848Notes

Reaction equation

HRID 1639848 reaction equation
[CH3:1][C:2]1[C:11]([N:12]=[S:13]=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].S(=NS(C)(=O)=O)=O.N1C=CC=CC=1.O>C1C=CC=CC=1>[N:12]1[S:13][CH:1]=[C:2]2[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[CH:10][C:11]=12

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 10931522Methanesulfonamide, N-sulfinyl-HCID 12255793Methyl 2-methyl-3-(sulfinylamino)benzoate

Product 1

HCID 12255806Methyl benzo[c]isothiazole-4-carboxylateYield 36.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of methyl 2-methyl-3-(sulfinylamino)benzoate (15.0 g, 71.0 mmol) in benzene (200 mL) was added a solution of N-sulfinylmethanesulfonamide (10.0 g, 71.0 mmol) and pyridine (9.19 mL, 114 mmol) in benzene (80 mL) at 0° C. The reaction mixture was heated under reflux for 18 hr, water was added, and the mixture was extracted with dichloromethane. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80) to give the title compound (5.0 g, yield 36%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 18 hr
  3. extractionthe mixture was extracted with dichloromethane
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80)

Sources & evidence

ORD record
ord-0f6111f19ae042aa8db898a4e83b324b
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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