Thiophenol → 2-Amino-5-phenylthio-1,3,4-thiadiazole

HRID 1073779Notes

Reaction equation

HRID 1073779 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[NH2:10][C:11]1[S:12][C:13](Br)=[N:14][N:15]=1>O.C(O)C>[NH2:10][C:11]1[S:12][C:13]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:14][N:15]=1

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 14797Potassium HydroxideHCID 36508832-Amino-5-bromo-1,3,4-thiadiazole

Product 1

HCID 146950682-Amino-5-phenylthio-1,3,4-thiadiazoleYield 79.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
82 °C

Procedure

In a mixture of 20 ml of water and 30 ml of ethanol, 7.3 g of thiophenol and 4.5 g of potassium hydroxide were added. To this solution, 11.7 g of 2-amino-5-bromo-1,3,4-thiadiazole was added, and the mixture was heated to 82° C. and stirred for 2 hours. After cooling, water was added and the mixture was filtered. The residue was washed with water and n-hexane respectively, dried under reduced pressure, and thus 10.8 g of 2-amino-5-phenylthio-1,3,4-thiadiazole was obtained. m.p. 202°~203° C. Yield 77%.

Workup

  1. additionwere added
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. washThe residue was washed with water and n-hexane respectively
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-34899434824746c1807ad518bddb1c91
Source dataset
uspto-grants-1990_11
Patent number
US04971971

Reaction notes

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