Hydrochloric Acid → 7-[[5-[(4-Acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazol-2-yl]thio]heptanoic acid

HRID 2107100Notes

Reaction equation

HRID 2107100 reaction equation
[C:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][S:9][C:10]2[S:11][C:12]([SH:15])=[N:13][N:14]=2)=[C:6]([CH2:18][CH2:19][CH3:20])[C:5]=1[OH:21])(=[O:3])[CH3:2].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.C(C(C)=O)C>[C:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][S:9][C:10]2[S:11][C:12]([S:15][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[N:13][N:14]=2)=[C:6]([CH2:18][CH2:19][CH3:20])[C:5]=1[OH:21])(=[O:3])[CH3:2]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 1217237-Bromoheptanoic acidHCID 178439538HCID 178439538, compound

Product 1

HCID 140531347-[[5-[(4-Acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazol-2-yl]thio]heptanoic acidYield 72.7%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 0.20 g of 2-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-5-mercapto-1,3,4-thiadiazole obtained in Example 8, 0.15 g of 7-bromoheptanoic acid, 0.18 g of anhydrous potassium carbonate and 5 ml of methyl ethyl ketone was added a catalytic amount of tetra-n-butylammonium bromide. The mixture was stirred at 60° C. for 1 hour. An aqueous sodium hydroxide solution and ethyl acetate were added to the reaction solution to perform fractionation. The aqueous phase was made acidic with 2N hydrochloric acid and extracted with ethyl acetate After the extract was dried over anhydrous magnesium sulfate, the solvent was distilled off. The residue was applied to silica gel column chromatography. Elution with a mixture of hexane-ethyl acetate (2:1) gave 0.20 g of 7-[[5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazol-2-yl]thio]heptanoic acid.

Workup

  1. extractionextracted with ethyl acetate After the extract
  2. dry with materialwas dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. washElution
  5. additionwith a mixture of hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-8ea001262f354e29b2a58b6e714957a6
Source dataset
uspto-grants-1990_06
Patent number
US04933348

Reaction notes

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