Hydrochloric Acid → HCID 178439538, compound

HRID 1646505Notes

Reaction equation

HRID 1646505 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:18][C:19]([SH:22])=[N:20][N:21]=1.C(=O)([O-])[O-].[K+].[K+].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(C(C)=O)C>[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][S:16][C:17]2[S:18][C:19]([SH:22])=[N:20][N:21]=2)=[C:6]([CH2:12][CH2:13][CH3:14])[C:5]=1[OH:15])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 137810224-Acetyl-3-hydroxy-2-propylbenzyl chlorideHCID 178418558HCID 178418558, compound

Product 1

HCID 178439538HCID 178439538, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 0.30 g of 4-acetyl-3-hydroxy-2-propylbenzyl chloride, 0.24 g of 2,5-dimercapto-1,3,4-thiadiazole, 0.20 g of anhydrous potassium carbonate and 4 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. After the reaction solution was rendered neutral by adding diluted hydrochloric acid thereto, it was extracted with ethyl acetate. After the extract was dried over anhydrous magnesium sulfate, the solvent was distilled off. The residue was recrystallized from isopropyl alcohol to give 0.20 g of 2-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-5-mercapto-1,3,4-thiadiazole.

Workup

  1. extractionit was extracted with ethyl acetate
  2. dry with materialAfter the extract was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customThe residue was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-4dac4224c4c6467e9323163fad06773c
Source dataset
uspto-grants-1993_01
Patent number
US05180730

Reaction notes

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