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Chemical Structure| 16182-04-0
Chemical Structure| 16182-04-0
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Product Details of [ 16182-04-0 ]

CAS No. :16182-04-0 MDL No. :MFCD00004814
Formula : C4H5NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :BDTDECDAHYOJRO-UHFFFAOYSA-N
M.W : 131.15 Pubchem ID :85320
Synonyms :

Safety of [ 16182-04-0 ]

Signal Word:Danger Class:6.1,3
Precautionary Statements:P210-P233-P240-P241-P242-P243-P261-P264-P271-P272-P280-P284-P303+P361+P353-P304+P340+P311-P305+P351+P338-P333+P313-P337+P313-P342+P311-P370+P378-P403+P233-P403+P235-P405-P501 UN#:2929
Hazard Statements:H226-H315-H317-H319-H331-H334-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 16182-04-0 ]

* 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 [ 16182-04-0 ]
  • Downstream synthetic route of [ 16182-04-0 ]

[ 16182-04-0 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 1147550-11-5 ]
  • [ 541-41-3 ]
  • [ 16182-04-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1457 - 1459
[2] Synthesis, 1983, # 6, p. 478 - 480
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 120 - 122
[4] Canadian Journal of Chemistry, 1981, vol. 59, p. 1557 - 1559
[5] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1986, vol. 41, # 1, p. 105 - 109
[6] Journal of the Indian Chemical Society, 1993, vol. 70, # 8, p. 671 - 674
[7] Collection of Czechoslovak Chemical Communications, 1996, vol. 61, # 1, p. 147 - 154
[8] Patent: WO2013/28818, 2013, A1, . Location in patent: Page/Page column 28; 29; 46; 47
  • 2
  • [ 541-41-3 ]
  • [ 16182-04-0 ]
Reference: [1] Phosphorus, Sulfur and Silicon and the Related Elements, 2010, vol. 185, # 1, p. 222 - 231
[2] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2012, vol. 93, p. 245 - 249
  • 3
  • [ 333-20-0 ]
  • [ 541-41-3 ]
  • [ 16182-04-0 ]
Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 17, p. 3407 - 3415
[2] Journal of the Chemical Society, 1908, vol. 93, p. 689
[3] Canadian Journal of Chemistry, 1975, vol. 53, p. 907 - 912
[4] Bulletin of the Chemical Society of Japan, 1963, vol. 36, # 9, p. 1214 - 1220
[5] Zeitschrift fuer Chemie (Stuttgart, Germany), 1988, vol. 28, # 5, p. 182 - 183
[6] Journal fuer Praktische Chemie (Leipzig), 1988, vol. 330, # 3, p. 383 - 390
[7] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1992, vol. 31, # 6, p. 370 - 372
[8] Synthetic Communications, 2004, vol. 34, # 12, p. 2205 - 2213
[9] Phosphorus, Sulfur and Silicon and the Related Elements, 2004, vol. 179, # 10, p. 2051 - 2057
[10] Journal of Chemical Research, 2004, # 4, p. 298 - 299
[11] Phosphorus, Sulfur and Silicon and the Related Elements, 2007, vol. 182, # 4, p. 863 - 871
[12] Journal of the American Chemical Society, 2008, vol. 130, # 44, p. 14456 - 14458
[13] Journal of the American Chemical Society, 2009, vol. 131, # 46, p. 16919 - 16926
[14] Organic Process Research and Development, 2014, vol. 18, # 1, p. 122 - 134
[15] Chemical Communications, 2014, vol. 50, # 85, p. 12873 - 12876
[16] Heterocycles, 2016, vol. 92, # 5, p. 829 - 843
[17] Patent: CN105399746, 2016, A, . Location in patent: Paragraph 0073-0074
[18] Patent: CN103739606, 2016, B, . Location in patent: Paragraph 0021; 0022; 0023
  • 4
  • [ 540-72-7 ]
  • [ 541-41-3 ]
  • [ 16182-04-0 ]
YieldReaction ConditionsOperation in experiment
99% With pyridine In water; toluene Example 1
Preparation of ethoxycarbonyl isothiocyanate
A 1-liter (L) jacketed reactor was charged with sodium thiocyanate (39.1 grams (g), 0.48 moles (mol)) and 310 g of toluene.
The solution was heated to 30° C. and treated with pyridine (0.4 g, 0.005 mol) and water (0.9 g, 0.05 mol).
Then ethyl chloroformate (52.9 g, 0.49 mol) was added drop-wise to the solution over 40 minutes (min).
The solution was left to stir for 3 hours (h), at which time nearly all the ethyl chloroformate had been consumed as determined by gas chromatography (GC).
The solution was then filtered and analyzed by GC affording the final product in 99percent yield as determined using a quantitative internal standard method.
63% With pyridine In water; toluene Comparative Example 2
Preparation of ethoxycarbonyl isothiocyanate with Minimal Water
A 1-L jacketed reactor was charged with sodium thiocyanate (39.1 g, 0.48 mol) and 310 g of toluene.
The solution was dried via vacuum distillation (70° C., 230 mmHg) until it contained approximately 50 ppm water as determined by Karl Fischer titration.
The solution was subsequently cooled to 30° C. and treated with pyridine (0.4 g, 0.005 mol).
Then ethyl chloroformate (52.9 g, 0.49 mol) was added drop-wise to the solution over 40 min.
The solution was left to stir for 22 h, at which time nearly all the ethyl chloroformate had been consumed as determined by GC.
The solution was then filtered and analyzed by GC affording the final product in 63percent yield as determined using a quantitative internal standard method.
Reference: [1] Patent: US2014/100381, 2014, A1, . Location in patent: Page/Page column
[2] Journal of Organic Chemistry, 1990, vol. 55, # 18, p. 5230 - 5231
[3] Research on Chemical Intermediates, 2012, vol. 38, # 3-5, p. 903 - 909
[4] Patent: US2014/100381, 2014, A1, . Location in patent: Page/Page column
[5] Journal of Organic Chemistry, 1990, vol. 55, # 18, p. 5230 - 5231
[6] Chinese Chemical Letters, 2012, vol. 23, # 1, p. 93 - 96
[7] Patent: CN108794427, 2018, A, . Location in patent: Paragraph 0031; 0033
  • 5
  • [ 541-41-3 ]
  • [ 16182-04-0 ]
Reference: [1] Patent: US4778921, 1988, A,
[2] Patent: US4123437, 1978, A,
  • 6
  • [ 541-41-3 ]
  • [ 99-56-9 ]
  • [ 16182-04-0 ]
Reference: [1] Patent: US4029813, 1977, A,
[2] Patent: US4020095, 1977, A,
  • 7
  • [ 64-17-5 ]
  • [ 78366-54-8 ]
  • [ 16182-04-0 ]
Reference: [1] Chemische Berichte, 1981, vol. 114, # 5, p. 1746 - 1751
  • 8
  • [ 541-41-3 ]
  • [ 592-87-0 ]
  • [ 16182-04-0 ]
Reference: [1] Journal of the Chemical Society, 1896, vol. 69, p. 329
  • 9
  • [ 1147550-11-5 ]
  • [ 79-03-8 ]
  • [ 16182-04-0 ]
Reference: [1] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983, vol. 38, # 6, p. 764 - 768
  • 10
  • [ 36315-01-2 ]
  • [ 16182-04-0 ]
  • [ 13223-43-3 ]
YieldReaction ConditionsOperation in experiment
91.1%
Stage #1: at 78℃; for 5.33333 h; Heating / reflux
Stage #2: With hydroxyammonium sulfate In water; ethyl acetate at 71℃; Heating / reflux
Stage #3: With sodium carbonate In water; ethyl acetate at 71℃; for 7 h; Heating / reflux
One pot procedure for the synthesis of 2-amino-5,7-dimethoxy [1,2, 4] triazolopyrimidine (ADTP) from 2-amino-4,6-dimethoxypyrimidine (ADP) 11. 9 g (0.075 mol) ADP was dissolved in 68 g ethyl acetate. 11 g (0.0825 mol) ethoxycarbonyl isothiocyanate was added within 20 min. at 78°C (no exotherm). The mixture was stirred over 5 h at reflux (78-79°C). 49.2 g (0.075 mol) hydroxylammonium sulfate (25 percent solution in water) were added and the mixture heated to 71°C (reflux aceotrope). 50 g (0.1 mol) diluted caustic soda (2 mot/1) was added within 1 h to establish the pH from 1.3 to 6.5 and hold at 6.5-7. 0 (offgas C02 and H2S, slightly exotherm). The mixture was stirred over 6 h under reflux (71°C) for reaction completion. The mixture was cooled down over night to 20°C. The product (ADTP) was filtrated and washed 3 times with each 25 g water to remove the salt (Na content after first wash 0.42 percent, after second 0.20 percent, after third 0.025 percent). Finally the solid ADTP was dried. Yield : 91.1 percent in respect to ADP, purity 95.3 percent (quantitative HPLC assay).
Reference: [1] Patent: WO2005/63753, 2005, A1, . Location in patent: Page/Page column 6
  • 11
  • [ 5049-61-6 ]
  • [ 16182-04-0 ]
  • [ 88002-33-9 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: at 20℃; for 18 h; Cooling with ice
Stage #2: With hydroxylamine hydrochloride; triethylamine In 1,4-dioxane; methanol; ethanol at 20℃; for 5 h; Reflux
Step 1. [l,2,4]triazolo[l,5-a]pyrazin-2-amine [0190] To a stirred solution of pyrazin-2-amine (25.0 g, 0.26 mol) in dioxane (300 mL) was added O- ethyl carbonisothiocyanatidate (37.90 g, 0.29 mol) dropwise under ice-water bath. After stirring for 18 hrs at rt, the mixture was concentrated. A mixture of TEA (109 mL, 0.78 mol) and hydroxylamine hydrochloride (72.50 g, 1.04 mol) in MeOH/EtOH (200 mL : 200 mL) was then added to the suspension The resulting mixture was stirred for 1 hr at rt, then the heated to reflux to afford a clear solution. After refluxing for additional 4 hs, the mixture was cooled to rt and concentrated to afford the crude which was recrystallized with 95percent ethanol to afford the title compound as a pale yellow solid (32.03 g, 91percent). MS (ESI) calcd for C5H5N5: 135.1; found: 136.3 [M+H]. *H NM (400 MHz, d6- DMSO) δ 8.83 (d, J = 1.2 Hz, 1H), 8.68 (dd, J = 4.4 and 1.2 Hz, 1H), 7.97 (d, J = 4.4 Hz, 1H), 6.45 (brs, 2H).
33%
Stage #1: at 20℃; for 18 h;
Stage #2: With hydroxylamine hydrochloride; triethylamine In methanol; ethanol at 20℃; for 6 h; Reflux
To a solution of pyrazin-2-amine (2S g, 260 mmol)in dioxane (300 ml) at room temperature was added ethoxycarbonyl-isothiocyanate (37.9 g, 289 mmol) slowly. The mixturewas stirred for 18 hours and the solvent was evaporatedunder vacuum. The residual solid was dissolved in a mixtureof methanol (1SO ml) and ethanol (1SO ml). To this solutionwas added TEA (109 ml, 780 mmol) and hydroxylaminehydrochloride (72.S g, 1040 mmol). The mixture was stirredat room temperature for 2 hours and was heated to reflux for4 hours. The crude mixture was cooled to room temperatureand the solvent was evaporated. The residual solid was purifiedby colunm chromatography (0-20percent methanol/ClLx.'L)to obtain a white solid (60 g). The solid was taken into EtOAcand water. The aqueous layer was extracted with EtOActwice. The combined organic layer was washed with brineand dried over sodium sulfate to obtain [I ,2,4]triazolo[1 ,S-a]pyrazin-2-amine as a white solid (12 g, 88 mmol, 33percent).
Reference: [1] Patent: WO2016/100349, 2016, A2, . Location in patent: Paragraph 0190
[2] Patent: JP5714745, 2015, B2, . Location in patent: Paragraph 0535; 0536
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 9, p. 3687 - 3706
  • 12
  • [ 16182-04-0 ]
  • [ 6960-17-4 ]
  • [ 219715-62-5 ]
YieldReaction ConditionsOperation in experiment
70.4%
Stage #1: at 27 - 87℃;
Stage #2: at 40℃;
Stage #3: With hydroxylamine In water; toluene at 68 - 81℃;
Example 4
Preparation of 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine (Ia)
To a 700 mL jacketed vessel equipped with a mechanical stirrer, a dual pH/temperature probe, a nitrogen inlet, and a reflux condenser was added sequentially 27.9 g (0.180 mol) of 4-amino-2,5-dimethoxypyrimidine followed by 165.4 g (0.207 mol) of 16.4 wt percent ethoxy carbonylisothiocyanate solution in toluene.
The reaction mixture was heated to gentle reflux (87 ° C.) for 7 h at which time liquid chromatographic (LC) analysis indicated ˜95percent conversion of starting 4-amino-2,5-dimethoxypyrimidine.
The reaction mixture was cooled to 27 ° C. and allowed to stand overnight.
The mixture was heated to 40° C. and then 114.2 g (6.34 mol) of deionized water was added to the mixture.
After heating to reflux (˜68° C.).
, 14.3 g (0.217 mol) of a 50 wt percent aqueous hydroxylamine solution was continuously added over a 2 h 15 min period via a peristaltic pump.
During the course of the amine addition, the reaction pH rose from 4.44 to 6.95.
After complete addition of hydroxylamine, the pump line was flushed with 4.8 g (0.266 mol) of deionized water, the reaction mixture was heated to 81° C., and then stirred an additional 3 h during which time the reaction pH naturally raised to 7.40.
The reaction mixture was cooled to ambient temperature (26° C.).
The reaction mixture was then suction transferred into a temporary holding vessel.
The reactor was washed with two 30 g portions of water.
These water washes were combined with the reaction mixture.
The combined mixture was suctioned filtered through a coarse Buchner funnel (filtration time about 30 seconds), and the filtrate was collected and filtered a second time through the cake.
A final displacement cake wash with ˜40 g of methanol was performed and the product was dried at 60° C. under vacuum (˜<10 mm Hg; 1333 Pa) to afford 25.37 g of 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine as a light cream colored solid. NMR analysis (using benzyl acetate as an internal standard) indicated an 97.3percent purity of 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine active which corresponds to a 70.4percent yield.
Reference: [1] Patent: US2014/81024, 2014, A1, . Location in patent: Paragraph 0027
  • 13
  • [ 13534-99-1 ]
  • [ 16182-04-0 ]
  • [ 1124382-72-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5243 - 5254
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