Potassium Iodide → HCID 14053129, compound

HRID 1646503Notes

Reaction equation

HRID 1646503 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].[NH2:16][C:17]1[S:18][C:19]([SH:22])=[N:20][N:21]=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>[NH2:16][C:17]1[S:18][C:19]([S:22][CH2:8][C:7]2[CH:10]=[CH:11][C:4]([C:1](=[O:3])[CH3:2])=[C:5]([OH:15])[C:6]=2[CH2:12][CH2:13][CH3:14])=[N:20][N:21]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 137810224-Acetyl-3-hydroxy-2-propylbenzyl chlorideHCID 178509208HCID 178509208, compound

Product 1

HCID 14053129HCID 14053129, compoundYield 102.8%

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, 0.22 g of 2-amino-5-mercapto-1,3,4-thiadiazole, 0.22 g of anhydrous potassium carbonate and 3 ml of methyl ethyl ketone were added catalytic amounts of potassium iodide and tetra-n-butylammonium bromide followed by stirring at 60° C. for 2 hours. Ethyl acetate was added to the reaction mixture. After insoluble matters were filtered off, the filtrate was washed with an aqueous sodium hydroxide solution and then dried over anhydrous magnesium sulfate The solvent was then removed by distillation to give 0.44 g of 2-amino-5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazole.

Workup

  1. filtrationAfter insoluble matters were filtered off
  2. washthe filtrate was washed with an aqueous sodium hydroxide solution
  3. dry with materialdried over anhydrous magnesium sulfate The solvent
  4. customwas then removed by distillation

Sources & evidence

ORD record
ord-52d40289330243b695a05cd15299096c
Source dataset
uspto-grants-1993_01
Patent number
US05180730

Reaction notes

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