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Chemical Structure| 2349-67-9

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Product Details of 2-Amino-5-mercapto-1,3,4-thiadiazole

CAS No. :2349-67-9
Formula : C2H3N3S2
M.W : 133.20
SMILES Code : SC1=NN=C(N)S1
MDL No. :MFCD00003108
InChI Key :GDGIVSREGUOIJZ-UHFFFAOYSA-N
Pubchem ID :2723847

Safety of 2-Amino-5-mercapto-1,3,4-thiadiazole

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 2-Amino-5-mercapto-1,3,4-thiadiazole

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 2349-67-9 ]

[ 2349-67-9 ] Synthesis Path-Downstream   1~12

  • 2
  • [ 2349-67-9 ]
  • [ 74-88-4 ]
  • [ 5319-77-7 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; (2) 2-amino-5-mercapto-1,3,4-thiadiazole (4.0 mmol), potassium carbonate (6.0 mmol), DMF (2 mL) as a solvent, and placed in a 100 mL three-neck bottle. After stirring, the solid was dissolved, and iodomethane (4.0 mmol) was slowly added dropwise, followed by stirring at room temperature for 2-6 h. After the reaction was completed, the solvent was removed under reduced pressure, ice water was added, and then the solid was collected by filtration. Recrystallization from absolute ethanol to give the intermediate 2-amino-5-methylmercapto-1,3,4-thiadiazole.
  • 4
  • [ 2349-67-9 ]
  • [ 5319-77-7 ]
  • 6
  • [ 2349-67-9 ]
  • [ 5319-77-7 ]
YieldReaction ConditionsOperation in experiment
In potassium hydroxide; ethanol; water; dimethyl sulfate; Step 1 5-Amino-1,3,4-thiadiazole-2-thiol (10.1 g) is dissolved in 31 mL of 20% KOH in ethanol and 6.1 mL of water. This solution is cooled in an ice bath and stirred while dimethyl sulfate (7.7 mL) is added dropwise. The reaction is stirred in an ice bath for an additional hour and the filtered. The solid is washed with 50% ethanol/water and dried. Recrystallization from ethanol give 4.8 g of 5-amino-2-methylthio-1,3,4-thiadiazole.
  • 7
  • [ 2349-67-9 ]
  • methyl halide [ No CAS ]
  • [ 5319-77-7 ]
  • 8
  • [ 74-87-3 ]
  • [ 2349-67-9 ]
  • [ 5319-77-7 ]
  • 9
  • [ 74-83-9 ]
  • [ 2349-67-9 ]
  • [ 5319-77-7 ]
YieldReaction ConditionsOperation in experiment
General procedure: 5-Amino-1,3,4-thiadiazole-2-thiol 1 was dissolved in a mixture of NaOH in absolute EtOH. After 10 min, the corresponding benzyl chlorides (R-PhCH2-Cl) or bromine halogenated hydrocarbon (R-Br) was added dropwise with vigorous stirring at room temperature. The reaction was monitored by TLC and completed within 10 h. The mixture was poured into water, and the precipitate was washed with water to yield 2a-2s.
  • 10
  • [ 17641-08-6 ]
  • [ 2349-67-9 ]
  • 2-amino-5-[(3-methoxyphenylcarbamoyl)methylthio]-1,3,4-thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With sodium hydroxide; In ethanol; water; at 20℃; General procedure: A solution of sodium hydroxide (6 mmol) in water (20 mL) was added to a mixture of 2-amino-5-mercapto-1,3,4-thiadiazole (6 mmol), appropriate 2-chloro-N-(substituted phenyl)-acetamide (2a-q, 5 mmol) and ethanol (10 mL). The mixture was stirred for 4-5 h at room temperature (the end of reaction was monitored by TLC), after completion, the mixture was poured into water. The resulting precipitate was collected by filtration, washed well with water and further puried by recrystallization from ethanol to afford target compounds.
  • 11
  • [ 2349-67-9 ]
  • [ 17329-87-2 ]
  • 2-amino-5-[(4-nitrophenylcarbamoyl)methylthio]-1,3,4-thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With sodium hydroxide; In ethanol; water; at 20℃; General procedure: A solution of sodium hydroxide (6 mmol) in water (20 mL) was added to a mixture of 2-amino-5-mercapto-1,3,4-thiadiazole (6 mmol), appropriate 2-chloro-N-(substituted phenyl)-acetamide (2a-q, 5 mmol) and ethanol (10 mL). The mixture was stirred for 4-5 h at room temperature (the end of reaction was monitored by TLC), after completion, the mixture was poured into water. The resulting precipitate was collected by filtration, washed well with water and further puried by recrystallization from ethanol to afford target compounds.
  • 12
  • [ 23784-96-5 ]
  • [ 2349-67-9 ]
  • C7H6ClN3S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: Intermediate 2 was synthesized as detailed in a prior report [31] with minor modification.Intermediate 1 (3.8 mmol) and triethylamine (7.6 mmol) were added into 30 mL of pyridine.The mixture was incubated ambient temperature for 0.5 h. Then, bromoethane (3.9 mmol) was added tothe reaction system and the mixture was treated at room temperature for four h. After the reaction wascompleted (as indicated by TLC), 100 mL of deionized water was added to the mixture and left to standfor 10 min. The mixture was then filtered, and the solid was washed with water and subsequently driedunder vacuum. Intermediate 2a was obtained 0.55 g at a yield of 89%. m.p. 136-137 C. Intermediates 2b-2p were prepared following a similar procedure.
 

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