Potassium Iodide → Ethyl [[5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazol-2-yl]thio]acetate

HRID 1646500Notes

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][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[N:19][N:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.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][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[N:19][N:18]=2)=[C:6]([CH2:12][CH2:13][CH3:14])[C:5]=1[OH:15])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 0.42 g of 4-acetyl-3-hydroxy-2-propylbenzyl chloride, 0.54 g of ethyl [(5-mercapto-1,3,4-thiadiazol-2-yl)thio]acetate, 0.30 g of anhydrous potassium carbonate and 5 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 toluene 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 subjected to silica gel column chromatography. Elution with a mixture of hexane-ethyl acetate (5:1) gave 0.75 g of oily ethyl [[5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]1,3,4-thiadiazol-2-yl]thio]acetate. Nuclear magnetic resonance spectrum (in CDCl3,

Workup

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

Sources & evidence

ORD record: ord-512bdafb4884484d9bc56bd22b30d34d
Source dataset: uspto-grants-1993_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05180730

Reaction notes

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