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Chemical Structure| 188672-83-5
Chemical Structure| 188672-83-5
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Product Details of [ 188672-83-5 ]

CAS No. :188672-83-5 MDL No. :MFCD18813190
Formula : C8H3N3O2S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 205.19 Pubchem ID :-
Synonyms :

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Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 188672-83-5 ]

* 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 [ 188672-83-5 ]
  • Downstream synthetic route of [ 188672-83-5 ]

[ 188672-83-5 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 188672-83-5 ]
  • [ 7724-12-1 ]
YieldReaction ConditionsOperation in experiment
71% at 20℃; for 24 h; Iron powder (68.05 g, 1218.55 mmol) was added to a suspension of 6-nitro-1,3-benzothiazole-2-carbonitrile (13, 5.00 g,24.37 mmol) in acetic acid (500 mL). The reaction mixture was stirred at room temperature for 24 h, diluted with water (1 L)and unreacted iron was removed by filtration through celite.The aqueous solution was extracted with EtOAc (4 × 500 mL).The combined organic layers were washed with brine (2 ×300 mL), dried (Na2SO4) and concentrated in vacuo. The crudeproduct was loaded onto a short plug of silica gel, flushedthrough with CHCl3(ca. 1 L) and concentrated in vacuo to give8as yellow microcrystals (3.02 g, 17.24 mmol, 71percent). A sample of 13was crystallised from EtOH for melting point analysis.Rf0.2 (SiO2, DCM); mp 219–220 °C (EtOH); 1H NMR(500 MHz, CDCl3) δ7.95 (d, J= 8.9 Hz, 1H, CH-4), 7.08 (d, J= 2.2 Hz, 1H, CH-7), 6.95 (dd, J= 8.8, 2.2 Hz, 1H, CH-5), 4.14(s, 2H, NH2); 13C NMR (125 MHz, CDCl3) δ147.8 (C-6),145.7 (C-7a), 138.3 (C-3a), 131.2(C-2), 126.1 (CH-4), 117.8(CH-5), 113.7 (C≡N), 104.0 (CH-7).
Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 7, p. 2117 - 2121
[2] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2019 - 2025
[3] Patent: US2011/213124, 2011, A1,
[4] Patent: US2011/224442, 2011, A1, . Location in patent: Page/Page column 11
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  • [ 7724-12-1 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 27, p. 8656 - 8659
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