Potassium Iodide → HCID 14839458, compound

HRID 1646506Notes

Reaction equation

HRID 1646506 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[C:6]([CH2:12][CH2:13][CH3:14])[C:5]=1[OH:15])(=[O:3])[CH3:2].[SH:16][C:17]1[S:21][C:20]([S:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N:19][N:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.C(C(C)=O)C>[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][S:16][C:17]2[S:21][C:20]([S:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N:19][N:18]=2)=[C:6]([CH2:12][CH2:13][CH3:14])[C:5]=1[OH:15])(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 137810224-Acetyl-3-hydroxy-2-propylbenzyl chlorideHCID 178471526HCID 178471526, compound

Product 1

HCID 14839458HCID 14839458, compoundYield 83.8%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 0.30 g of 4-acetyl-3-hydroxy-2-propylbenzyl chloride, 0.39 g of ethyl 5-[(5-mercapto-1,3,4-thiadiazol-2-yl)thio]valerate, 0.20 g of anhydrous potassium carbonate and 4 ml of methyl ethyl ketone were added catalytic amounts of potassium iodide and tetra-n-butylammonium bromide followed by stirring at 60° C. for 3 hours The reaction mixture was diluted with ethyl acetate and insoluble matters were filtered off. The filtrate was washed with an aqueous sodium hydroxide solution and dried over anhydrous magnesium sulfate. The solvent was then distilled off. The residue was applied to silica gel column chromatography. Elution with a mixture of hexane-ethyl acetate (5:1) gave 0.52 g of oily ethyl 5-[[5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazol-2-yl]thio]valerate.

Workup

  1. filtrationwere filtered off
  2. washThe filtrate was washed with an aqueous sodium hydroxide solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was then distilled off
  5. washElution
  6. additionwith a mixture of hexane-ethyl acetate (5:1)

Sources & evidence

ORD record
ord-f127db1e65b44574b7f95ab1dda278c6
Source dataset
uspto-grants-1993_01
Patent number
US05180730

Reaction notes

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