Hydrochloric Acid → Benzoic acid, 4-(((5-(((4-acetyl-3-hydroxy-2-propylphenyl)methyl)thio)-1,3,4-thiadiazol-2-yl)thio)methyl)-

HRID 1646520Notes

Reaction equation

HRID 1646520 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][C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.CC(=O)CC>[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][C:24]3[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=3)=[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 225994-(Bromomethyl)benzoic acidHCID 178439538HCID 178439538, compound

Product 1

HCID 3065384Benzoic acid, 4-(((5-(((4-acetyl-3-hydroxy-2-propylphenyl)methyl)thio)-1,3,4-thiadiazol-2-yl)thio)methyl)-Yield 73.2%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 0.49 g of 2-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-5-mercapto-1,3,4-thiadiazole, 0.36 g of p-(bromomethyl)benzoic acid, 0.48 g of anhydrous potassium carbonate and 12 ml of 2-butanone was added a catalytic amount of tetra-n-butyl ammonium bromide followed by stirring at 60° C. for 45 minutes. An aqueous sodium hydroxide solution and ethyl acetate were added to the reaction mixture to fractionate. The aqueous phase was made acidic with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, the solvent was distilled off. The thus obtained solid was recrystallized from isopropyl alcohol to give 0.50 g of p-[[5-[(4-acetyl-3-hydroxy-2-propylbenzyl)-thio]-1,3,4-thiadiazol-2-yl]thiomethyl]benzoic acid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe thus obtained solid was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-070e7a24761848f7800385ae583e9d73
Source dataset
uspto-grants-1993_01
Patent number
US05180730

Reaction notes

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