3-Chloropropanesulphonyl chloride → 2-(4-Cyclopropylpiperazin-1-yl)-6-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)benzothiazole

HRID 1944684Notes

Reaction equation

HRID 1944684 reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[S:11][C:12]4[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.[H-].[Na+].Cl[CH2:23][CH2:24][CH2:25][S:26](Cl)(=[O:28])=[O:27]>CN(C=O)C>[CH:1]1([N:4]2[CH2:5][CH2:6][N:7]([C:10]3[S:11][C:12]4[CH:18]=[C:17]([N:19]5[CH2:23][CH2:24][CH2:25][S:26]5(=[O:28])=[O:27])[CH:16]=[CH:15][C:13]=4[N:14]=3)[CH2:8][CH2:9]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 154103-Chloropropanesulphonyl chlorideHCID 24758Sodium hydrideHCID 595888042-(4-Cyclopropylpiperazin-1-yl)benzothiazol-6-ylamine

Product 1

HCID 237289692-(4-Cyclopropylpiperazin-1-yl)-6-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)benzothiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-(4-cyclopropylpiperazin-1-yl)benzothiazol-6-ylamine (500 mg, 1.82 mmol) in DMF (10 mL) was added NaH (220 mg, 5.46 mmol) at 0° C. The mixture was allowed to warm to rt and then stirred for 30 min. A solution of 3-chloropropane-1-sulfonyl chloride (450 mg, 2.55 mmol) in DMF (2 mL) was added and the reaction mixture was stirred for 2 h. The resulting mixture was extracted with ethyl acetate (3×20 mL). The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure to give a residue which was purified by column chromatography on silica gel (elute: 2% dichloromethane in methanol). This afforded 217 mg (31%) of 2-(4-cyclopropylpiperazin-1-yl)-6-(1,1-dioxo-1λ6-isothiazolidin-2-yl)benzothiazole.

Workup

  1. stirringthe reaction mixture was stirred for 2 h
  2. extractionThe resulting mixture was extracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customto give a residue which
  6. customwas purified by column chromatography on silica gel (elute: 2% dichloromethane in methanol)

Sources & evidence

ORD record
ord-c5709ec0db384e128554a653a3531937
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

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