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Chemical Structure| 175136-67-1 Chemical Structure| 175136-67-1

Structure of 175136-67-1

Chemical Structure| 175136-67-1

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Product Details of [ 175136-67-1 ]

CAS No. :175136-67-1
Formula : C4H5N3OS
M.W : 143.17
SMILES Code : O=C(C1=C(C)N=NS1)N
English Name :4-Methyl-1,2,3-thiadiazole-5-carboxamide
MDL No. :MFCD00052214

Safety of [ 175136-67-1 ]

Application In Synthesis of [ 175136-67-1 ]

* 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 [ 175136-67-1 ]

[ 175136-67-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 60-29-7 ]
  • [ 18212-21-0 ]
  • [ 175136-67-1 ]
YieldReaction ConditionsOperation in experiment
85% With ammonia In tetrahydrofuran; thionyl chloride; hexane; dichloromethane; ethyl acetate 13.B Step B Step B A suspension of 4-methyl[1,2,3]thiadiazole-5-carboxylic acid (1.65 g; 11.44 mmol), obtained as described in the above step, in SOCl2 (10 ml) was refluxed for 2.5 hours. After concentration of the solution under vacuum, the residue was taken up a few times in CH2Cl2, evaporating each time. The oily residue obtained (1.9 g; 11.44 mmol) was dissolved in anhydrous THF (30 ml) and the solution was added dropwise and cautiously to a mixture of NH3 gas in THF (150 ml), cooled to 0° C. After the dropwise addition, the reaction mixture was stirred for 30 minutes at room temperature. The solvent was evaporated off and the residue was taken up in a mixture of ethyl acetate and saline solution. The phases were separated and the aqueous phase was extracted twice more with ethyl acetate. The combined organic extracts, washed once with saline solution, were dried and concentrated under vacuum. The solid residue obtained was triturated from a 20/80 ethyl ether/hexane mixture to give 4-methyl[1,2,3]thiadiazole-5-carboxamide (1.4 g; 85% yield) as a pale yellow solid. 1H-NMR (DMSO) δ: 8.21-8.03 (2 broad signals, 2H, NH2); 2.78 (s, 3H, CH3).
  • 2
  • [ 18212-21-0 ]
  • [ 175136-67-1 ]
YieldReaction ConditionsOperation in experiment
59% With dmap; N,O-dimethylhydroxylamine*hydrochloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 3h; Cooling with ice; 2 Example 2: Preparation of Compound II Method 2: Add 50.50 mmol to a 100 ml single-mouth round bottom flask.Ie 10 g of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid, 20 ml of dry dichloromethane,Then add 1.1 equivalents of triethylamine dropwise, stir, after the solution is clarified,50.50 mmol of O,N-dimethylhydroxylamine hydrochloride was added under ice water bath.Then divide it 10 times and add 55.55 millimoles of EDCI in 20 minutes.8.58 mmol of DMAP was added and stirred at room temperature for 3 h. TLC monitors the extent of the reaction,After the reaction was completed, the mixture was filtered, and the filtrate was taken, washed twice with water and twice with saturated brine.The layers were back-extracted with dichloromethane (20 mL × 3).Concentration, the residue is purified by silica gel column chromatography from 200 to 300 mesh.The eluent is petroleum ether: ethyl acetate at 60-90 degrees Celsius, and the volume ratio is 8:1.The yield was 59%.
Stage #1: 4-methyl-[1,2,3]thiadiazole-5-carboxylic acid With thionyl chloride for 0.6h; Reflux; Stage #2: With ammonia 6 In 100 ml round-bottom flask, by adding intermediate 4-methyl -1, 2, 3-thiadiazol-5-carboxylic acid 2.0 g, in other words, 13.87 mmol, then adding thionyl chloride 10.0 g, in other words, 83.2 mmol, reflux reaction is about 6 hours; distillation to remove the surplus thionyl chloride; ammonia slowly adding 0.47 g, in other words, 27.7 mmol, prepared 4-methyl -1, 2, 3-thiadiazol-5-carboxamide;
  • 3
  • [ 175136-67-1 ]
  • [ 18212-21-0 ]
YieldReaction ConditionsOperation in experiment
93.01% With bromine; sodium hydroxide In water at 70℃; Cooling with ice; 6 F. Synthesis of Intermediate substituted 5-amino -1, 2, 3-thiadiazole VIIB In 100 ml round-bottom flask, by adding intermediate 4-methyl -1, 2, 3-thiadiazol-5-carboxylic acid 2.0 g, in other words, 13.87 mmol, then adding thionyl chloride 10.0 g, in other words, 83.2 mmol, reflux reaction is about 6 hours; distillation to remove the surplus thionyl chloride; ammonia slowly adding 0.47 g, in other words, 27.7 mmol, prepared 4-methyl -1, 2, 3-thiadiazol-5-carboxamide; In 100 ml round-bottom flask, add 17 ml of water with sodium hydroxide 1.68 g, in other words, 42.0 mmol, under the condition of ice bath slowly instillment bromine 1.34 g, in other words, 8.38 millimole; the drop finishes insulation reaction after 30 minutes, sodium bromate once prepared, then batch by adding 1.0 g of the intermediate amide, stirring for about 1 hour, removed ice-bath, heated to the 70 degree Celcius reaction, solid all dissolved; TLC detection reaction is complete after adding concentrated hydrochloric acid to the system, until a white solid precipitated; filter to get the solid, the filtrate is extracted with ethyl acetate, the organic layer is dried with anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, get white intermediate solid merger VIIB 0.75 g, yield 93.01% ; in order to 5-chloro -1, 2, 3-thiadiazol-4-carboxylic acid, 5-methyl -1, 2, 3-thiadiazol-4-carboxylic acid, 1, 2, 3-thiadiazol-4-carboxylic acid, 4-cyclopropyl -1, 2, 3-thiadiazol-5-carboxylic acid instead of 4-methyl -1, 2, 3-thiadiazol-5-carboxylic acid can be used for preparing 4-amino-5-chloro -1, 2, 3-thiadiazole, 4-amino-5-methyl -1, 2, 3-thiadiazole, 4-amino -1, 2, 3-thiadiazole, 4-cyclopropyl-5-amino -1, 2, 3-thiadiazole.
 

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