Potassium Iodide → 3-{4-[2-(4-Nitro-phenoxy)-ethyl]-piperazin-1-YL}-1,2-benzisothiazole

HRID 2211863

Reaction equation

HRID 2211863 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[N:8]1([C:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[S:16][N:15]=2)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[I-].[K+].Cl[CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=1>C(#N)C>[N+:35]([C:32]1[CH:33]=[CH:34][C:29]([O:28][CH2:27][CH2:26][N:11]2[CH2:12][CH2:13][N:8]([C:14]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[S:16][N:15]=3)[CH2:9][CH2:10]2)=[CH:30][CH:31]=1)([O-:37])=[O:36]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27645871-(2-Chloroethoxy)-4-nitrobenzeneHCID 115217113-(1-Piperazinyl)-1,2-benzisothiazole monohydrochloride

Product 1

HCID 219633113-{4-[2-(4-Nitro-phenoxy)-ethyl]-piperazin-1-YL}-1,2-benzisothiazoleYield 114.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

Excess dried, −325 mesh potassium carbonate (257 mg, 1.86 mmol) was diluted in 4 mL acetonitrile and 3-piperazin-1-yl-benzoisothiazole hydrochloride (395 mg, 1.55 mmol), catalytic potassium iodide, and 1(2-chloroethoxy)-4-nitrobenzene (250 mg, 1.20 mmol) were added. This mixture was sealed in a Smith microwave vial and heated on the Smith Workstation at 150° C. for 1.5 h. After cooling, the salts were filtered off and washed with acetonitrile and the filtrate was concentrated. The residue was taken up in methylene chloride and washed with water. The organic layer was dried over sodium sulfate, and concentrated to afford 530 mg of a yellow solid. Yield 89%; 92% HPLC purity at 214 nm; mp 115° C.; MS (APCI): 385 [M+H]+.

Workup

  1. customThis mixture was sealed in a Smith microwave vial
  2. temperatureAfter cooling
  3. filtrationthe salts were filtered off
  4. washwashed with acetonitrile
  5. concentrationthe filtrate was concentrated
  6. washwashed with water
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cee48d3671df4eb092abef4a301d4b0a
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Linked notes

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