Potassium Iodide → HCID 21963474, compound

HRID 2211904Notes

Reaction equation

HRID 2211904 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[C:6]([F:14])[CH:5]=1.Cl.[N:16]1([C:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[S:24][N:23]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[S:24]1[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:22]([N:16]2[CH2:17][CH2:18][N:19]([CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[C:6]([F:14])[CH:5]=3)[CH2:20][CH2:21]2)=[N:23]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 115217113-(1-Piperazinyl)-1,2-benzisothiazole monohydrochlorideHCID 21963517HCID 21963517, compound

Product 1

HCID 21963474HCID 21963474, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-[4-(2-Bromo-ethyl)-2-fluoro-phenyl]-acetamide (0.2609 g, 1.00 mmol), 3-piperazin-1-yl-benzo[d]isothiazole hydrochloride (0.3887 g, 1.52 mmol), potassium carbonate (0.2109 g, 1.53 mmol), potassium iodide (0.1662 g, 1.00 mmol) and acetonitrile (5.0 mL) were added to a Smith microwave reaction tube containing a magnetic stir bar and then crimped shut. The reaction was run on a Smith Personal Chemistry microwave at 140° C. for 0.5 h. After removing the crimped septum, the contents were transferred to a separatory funnel with water (10 mL) and extracted with methylene chloride (2×40 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated to give an oily residue. Purification by MPLC on a 40M silica gel cartridge using a linear gradient over 1 h of 0–3% methanol in methylene chloride provided 0.1230 g (0.309 mmol) of the product as an off-white solid after drying in vacuo. Several fractions containing product and a by-product (0.1487 g total) were discarded. Yield: 31%; MS (APCI): 399.2 [M+H]+; Anal. Calcd. For C21H23FN4OS.0.25 H2O: C, 62.59; H, 5.88; N, 13.90. Found: C, 62.72; H, 5.53; N, 13.53.

Workup

  1. additioncontaining a magnetic stir bar
  2. customAfter removing the crimped septum
  3. customthe contents were transferred to a separatory funnel with water (10 mL)
  4. extractionextracted with methylene chloride (2×40 mL)
  5. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give an oily residue
  9. customPurification by MPLC on a 40M silica gel cartridge
  10. customover 1 h

Sources & evidence

ORD record
ord-bfc72c4245f241a083a092243ffae79e
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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