Potassium Carbonate → 2,1-Benzisothiazole, 4-chloro-1,3-dihydro-, 2,2-dioxide

HRID 429246Notes

Reaction equation

HRID 429246 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9](Cl)[C:3]=1[CH2:4][S:5]([NH2:8])(=[O:7])=[O:6].C(=O)([O-])[O-].[K+].[K+]>[Cu].CN(C)C1C=CC=CC=1>[O:6]=[S:5]1(=[O:7])[CH2:4][C:3]2[C:2]([Cl:1])=[CH:12][CH:11]=[CH:10][C:9]=2[NH:8]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 13631936(2,6-Dichlorophenyl)methanesulfonamide

Product 1

HCID 217951722,1-Benzisothiazole, 4-chloro-1,3-dihydro-, 2,2-dioxideYield 59%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 949N,N-DimethylanilineSolvent

Conditions

Temperature
170 °C

Procedure

The 2,6-dichlorobenzylsulfonamide (8 g, 33.47 mmol) was added to potassium carbonate (4.62 g, 33.47 mmol), copper powder (560 milligrams (hereinafter“mg”)) and N,N-dimethylaniline (10 ml) in flask. The reaction mixture was stirred at 170° C. for 4 hours, then it was cooled to room temperature and partitioned between ethyl acetate and 10% aqueous HCl. The combined organic phase was dried and concentrated. Chromatography of the residue on silica gel (30% Ethyl acetate/Hexane) gave desired product (4 g, 59%). MS(EI) m/e 204.5 (M+).

Workup

  1. temperatureit was cooled to room temperature
  2. custompartitioned between ethyl acetate and 10% aqueous HCl
  3. customThe combined organic phase was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-69c253cb904349349376c9b1aa729f0f
Source dataset
uspto-grants-2001_11
Patent number
US06316478B1

Reaction notes

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