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Product Details of Methyl 1H-1,2,4-triazole-5-carboxylate

CAS No. :4928-88-5
Formula : C4H5N3O2
M.W : 127.10
SMILES Code : O=C(C1=NNC=N1)OC
MDL No. :MFCD00135989
InChI Key :QMPFMODFBNEYJH-UHFFFAOYSA-N
Pubchem ID :2735089

Safety of Methyl 1H-1,2,4-triazole-5-carboxylate

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

Application In Synthesis of Methyl 1H-1,2,4-triazole-5-carboxylate

* 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.

  • Upstream synthesis route of [ 4928-88-5 ]
  • Downstream synthetic route of [ 4928-88-5 ]

[ 4928-88-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 4928-88-5 ]
  • [ 74-88-4 ]
  • [ 57031-66-0 ]
YieldReaction ConditionsOperation in experiment
34%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1 h; Inert atmosphere
Stage #2: at 20℃;
1003101 Step A: Preparation of methyl 1-methyl-1H-1,2,4-triazole-3-carboxylate: To a stirred suspension of Nail (60percent oil dispersion, 0.346 g, 8.66 mmol) in DMF (20 mL) was added dropwise a solution of methyl 1H-1,2,4-triazole-3-carboxylate (1.00 g, 7.87 mmol) in DMF (20 mE) at 0 °C under nitrogen. The reaction mixture was stirred at 0 °C for 1 hour. Mel (0.982 mL, 15.7 mmol) was added dropwise. The reaction mixture was stirred at ambient temperature overnight. The reaction was poured into cold water and extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by column chromatography (3:1 hexanes/EtOAc) to give the title compound (0.380 g, 34percent yield) as a white solid. MS (apci) mlz = 142.1 (M+H).
34%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1 h; Inert atmosphere
Stage #2: at 20℃;
[00430] Step A: Preparation of methyl l-methyl-lH-L2,4-triazole-3-carboxylate: To a stirred suspension of NaH (60percent oil dispersion, 0.346 g, 8.66 mmol) in DMF (20 mL) was added dropwise a solution of methyl lH-l,2,4-triazole-3-carboxylate (1.00 g, 7.87 mmol) in DMF (20 mL) at 0 °C under nitrogen. The reaction mixture was stirred at 0 °C for 1 hour. Mel (0.982 mL, 15.7 mmol) was added dropwise. The reaction mixture was stirred at ambient temperature overnight. The reaction was poured into cold water and extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by column chromatography (3: 1 hexanes/EtOAc) to give the title compound (0.380 g, 34percent yield) as a white solid. MS (apci) m/z = 142.1 (M+H).
34%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1 h; Inert atmosphere
Stage #2: at 20℃;
[00614] Step A: Preparation of methyl 1-methyl-1H-1,2,4-triazole-3-carboxylate: To a stirred suspension of NaH (60percent oil dispersion, 0.346 g, 8.66 mmol) in DMF (20 mL) was added dropwise a solution of methyl 1H-1,2,4-triazole-3-carboxylate (1.00 g, 7.87 mmol) in DMF (20 mE) at 0 °C under nitrogen. The reaction mixture was stirred at 0 °C for 1 hour. Mel (0.982 mL, 15.7 mmol) was added dropwise. The reaction mixture was stirred at ambient temperature overnight. The reaction was poured into cold water and extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by column chromatography (3:1 hexanes/EtOAc) to give the title compound (0.380 g, 34percent yield) as a white solid. MS (apci) m/z = 142.1 (M+H).
References: [1] Chemistry and Biodiversity, 2017, vol. 14, # 12, .
[2] Patent: WO2014/78417, 2014, A1, . Location in patent: Paragraph 00310.
[3] Patent: WO2014/78322, 2014, A1, . Location in patent: Paragraph 00430.
[4] Patent: WO2014/78325, 2014, A1, . Location in patent: Paragraph 00614.
 

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