Potassium Iodide → HCID 15725742, compound

HRID 1460703Notes

Reaction equation

HRID 1460703 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:10]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:9]1.[SH:31][CH2:32][C:33]([O:35][CH3:36])=[O:34].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CCCCCC.C(OCC)(=O)C.C(#N)C>[C:25]1([C:10]2[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][S:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])[N:9]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 15725741HCID 15725741, compound

Product 1

HCID 15725742HCID 15725742, compoundYield 95.4%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(6-bromohexyl)-3,4,5-triphenyl-1H-pyrazole (6.53 g, 14 mmol), methyl mercaptoacetate (1.66 g, 15 mmol), potassium carbonate (2.26 g, 16.5 mmol), potassium iodide (catalytic amount) and acetonitrile (150 mL) was heated at reflux for 4 hours. The mixture was cooled, filtered and concentrated in vacuo to give an oil. Chromatography on a column of silica gel using a mixture of hexane and ethyl acetate (4:1) as eluent furnished methyl [[6-(3,4,5-triphenyl-1H-pyrazol-1-yl)hexyl]thio]acetate (6.47 g, 91%) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an oil

Sources & evidence

ORD record
ord-44d31f4ccc044d2489b442a2dfb677ed
Source dataset
uspto-grants-1991_12
Patent number
US05071866

Reaction notes

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