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

HRID 1381574Notes

Reaction equation

[C:1]([C:4]1[CH:23]=[CH:22][C:7]([CH2:8][S:9][C:10]2[S:14][C:13]([S:15][CH2:16][C:17]([O:19]CC)=[O:18])=[N:12][N:11]=2)=[C:6]([CH2:24][CH2:25][CH3:26])[C:5]=1[OH:27])(=[O:3])[CH3:2].[OH-].[Na+].C(OCC)(=O)C.Cl>CO>[C:1]([C:4]1[CH:23]=[CH:22][C:7]([CH2:8][S:9][C:10]2[S:14][C:13]([S:15][CH2:16][C:17]([OH:19])=[O:18])=[N:12][N:11]=2)=[C:6]([CH2:24][CH2:25][CH3:26])[C:5]=1[OH:27])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

In 7.8 ml of 90% methanol was dissolved 0.98 g of ethyl [[5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazol-2-yl]thio]acetate obtained in Example 1 with heating at 60° C. Further 6.1 ml of a 1N aqueous sodium hydroxide solution was added to the solution followed by stirring at 60° C. for 30 minutes. A 1N aqueous sodium hydroxide solution and ethyl acetate were added to the reaction mixture to fractionate. The aqueous phase was made acidic with a 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with, in sequence, water, a saturated aqueous sodium chloride solution and water and then, dried over anhydrous magnesium sulfate. The solvent was then distilled off. Recrystallization of the thus obtained solid from isopropyl alcohol gave 0.75 g of [[5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazol-2-yl]thio]acetic acid.

Workup

extractionextracted with ethyl acetate
washThe extract was washed with, in sequence, water
dry with materiala saturated aqueous sodium chloride solution and water and then, dried over anhydrous magnesium sulfate
distillationThe solvent was then distilled off
customRecrystallization of the thus obtained solid from isopropyl alcohol

Sources & evidence

ORD record: ord-f313f4d8e9f546babc2dd70833b57e6b
Source dataset: uspto-grants-1989_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04803211

Reaction notes

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