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Chemical Structure| 16182-04-0 Chemical Structure| 16182-04-0

Structure of 16182-04-0

Chemical Structure| 16182-04-0

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Product Details of [ 16182-04-0 ]

CAS No. :16182-04-0
Formula : C4H5NO2S
M.W : 131.15
SMILES Code : O=C(N=C=S)OCC
MDL No. :MFCD00004814
InChI Key :BDTDECDAHYOJRO-UHFFFAOYSA-N
Pubchem ID :85320

Safety of [ 16182-04-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H226-H315-H317-H319-H331-H334-H335
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
Class:6.1(3)
UN#:2929
Packing Group:

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   1~2

  • 1
  • [ 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).
References: [1] Patent: WO2005/63753, 2005, A1, . Location in patent: Page/Page column 6.
  • 2
  • [ 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.
References: [1] Patent: US2014/81024, 2014, A1, . Location in patent: Paragraph 0027.
 

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