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[ CAS No. 5464-79-9 ]

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Chemical Structure| 5464-79-9
Chemical Structure| 5464-79-9
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CAS No. :5464-79-9 MDL No. :MFCD00005792
Formula : C8H8N2OS Boiling Point : 347.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :180.23 g/mol Pubchem ID :21622
Synonyms :

Safety of [ 5464-79-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302+H312+H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5464-79-9 ]

  • Upstream synthesis route of [ 5464-79-9 ]
  • Downstream synthetic route of [ 5464-79-9 ]

[ 5464-79-9 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 5464-79-9 ]
  • [ 7405-23-4 ]
Reference: [1] Arzneimittel-Forschung, 1980, vol. 30, # 11, p. 1831 - 1838
  • 2
  • [ 5464-79-9 ]
  • [ 7471-03-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 21, p. 6199 - 6202
[2] Ukrainskii Khimicheskii Zhurnal (Russian Edition), 1955, vol. 21, p. 344[3] Chem.Abstr., 1955, p. 14738
[4] Patent: US2002/173490, 2002, A1,
[5] Patent: US6756360, 2004, B1, . Location in patent: Page column 179
[6] Patent: WO2005/54249, 2005, A1, . Location in patent: Page/Page column 30-31
[7] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 14, p. 3614 - 3622
[8] Patent: US6489476, 2002, B1,
  • 3
  • [ 5464-79-9 ]
  • [ 7471-03-6 ]
Reference: [1] Patent: US2003/73728, 2003, A1,
  • 4
  • [ 1516-37-6 ]
  • [ 5464-79-9 ]
YieldReaction ConditionsOperation in experiment
94.08% at 40℃; for 17 h; Compound 3 (3.76 g, 0.02 mol) was dissolved in acetic acid (36 ml). To which was added lithium bromide (2.6 g, 0.03 mol) at room temperature, and bromine (1 ml, 0.02 mol) was slowly added dropwise in an ice bath, and then heated to 40° C., stirred for 17 h. The reaction system was lowered to room temperature and kept for 2 h. The reaction solution was filtered by suction and washed with acetic acid, and dried in a vacuum oven to give a white solid 4 (3.5 g, 94.08percent).
Reference: [1] Patent: US2016/102066, 2016, A1, . Location in patent: Paragraph 0021; 0025; 0027
[2] Medicinal Chemistry Research, 2012, vol. 21, # 7, p. 1136 - 1148
[3] Helvetica Chimica Acta, 1942, vol. 25, p. 515,519
[4] Yakugaku Zasshi, 1940, vol. 60, p. 462,473; dtsch. Ref. S. 184, 189[5] Chem.Abstr., 1941, p. 452
[6] Bulletin de la Societe Chimique de France, 1956, p. 684,688
[7] Heterocycles, 1980, vol. 14, # 8, p. 1145 - 1149
[8] Acta Poloniae Pharmaceutica - Drug Research, 2009, vol. 66, # 4, p. 387 - 392
[9] Patent: US2011/152246, 2011, A1, . Location in patent: Page/Page column 183
[10] Journal of Heterocyclic Chemistry, 2011, vol. 48, # 6, p. 1351 - 1355
[11] Chemical Biology and Drug Design, 2016, p. 354 - 362
[12] Journal of Medicinal Chemistry, 2016, vol. 59, # 21, p. 9814 - 9824
  • 5
  • [ 90-04-0 ]
  • [ 5464-79-9 ]
YieldReaction ConditionsOperation in experiment
74%
Stage #1: at 10℃;
Stage #2: at 10 - 20℃; for 4 h;
General procedure: A mixture of aniline (0.05mol) and NH4SCN (19.03g, 0.25mol) in glacial acetic acid (100mL) was cooled to 10°C in an ice bath and stirred for 10–20min. Then bromine (2.82mL, 0.055mol) in glacial acetic acid was added drop wise at such a rate to keep the temperature below 10°C. The mixture was stirred at room temperature for 4h and then poured into hot water (500mL), and basified to pH 11.0 with ammonia solution (NH4OH). The resulting precipitate was filtered, washed with water and dried to get a light yellow to brown solid. The crude product was purified by chromatography on silica gel using MeOH/CH2Cl2 to afford compounds 2a–2k in good yields.
Reference: [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1759 - 1775
[2] Gazzetta Chimica Italiana, 1964, vol. 94, p. 372 - 381
[3] Chemistry of Heterocyclic Compounds, 2009, vol. 45, # 11, p. 1343 - 1353
  • 6
  • [ 90-04-0 ]
  • [ 5464-79-9 ]
Reference: [1] Heterocycles, 1980, vol. 14, # 8, p. 1145 - 1149
[2] Patent: US2011/152246, 2011, A1,
[3] Journal of Heterocyclic Chemistry, 2011, vol. 48, # 6, p. 1351 - 1355
[4] Patent: US2016/102066, 2016, A1,
[5] Chemical Biology and Drug Design, 2016, p. 354 - 362
[6] Journal of Medicinal Chemistry, 2016, vol. 59, # 21, p. 9814 - 9824
  • 7
  • [ 1147550-11-5 ]
  • [ 90-04-0 ]
  • [ 5464-79-9 ]
Reference: [1] Medicinal Chemistry Research, 2011, vol. 20, # 7, p. 1033 - 1041
[2] European Journal of Medicinal Chemistry, 2018, vol. 148, p. 477 - 486
  • 8
  • [ 333-20-0 ]
  • [ 90-04-0 ]
  • [ 5464-79-9 ]
Reference: [1] Synlett, 2012, vol. 23, # 15, p. 2219 - 2222
  • 9
  • [ 134-29-2 ]
  • [ 5464-79-9 ]
Reference: [1] Medicinal Chemistry Research, 2012, vol. 21, # 7, p. 1136 - 1148
  • 10
  • [ 67-66-3 ]
  • [ 7726-95-6 ]
  • [ 1516-37-6 ]
  • [ 5464-79-9 ]
Reference: [1] Helvetica Chimica Acta, 1942, vol. 25, p. 515,519
[2] Yakugaku Zasshi, 1940, vol. 60, p. 462,473; dtsch. Ref. S. 184, 189[3] Chem.Abstr., 1941, p. 452
  • 11
  • [ 5464-79-9 ]
  • [ 3507-27-5 ]
YieldReaction ConditionsOperation in experiment
69% With copper dichloride; isopentyl nitrite In acetonitrile at 65℃; for 2 h; Inert atmosphere A 500 mL three-necked flask equipped with a condenser under nitrogen was charged with copper(II) chloride (3.36 g, 25.0 mmol), MeCN (71 mL) and isopentyl nitrite (2.2 mL, 16.6 mmol). The suspension was stirred in a 65 °C oil bath for 10 mm before adding a solution of 2- amino-4-methoxybenzothiazole (2.00 g, 11.1 mmol) in MeCN (42 mL). The reaction mixture was stirred in a 65 °C oil bath for 2 h and it was allowed to cool down at 20 °C. Water (150 mL) and iN HC1 (100 mL) were added and the resulting mixture was extracted with EtOAc (3 x 100 mL). Combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The obtained residue was purified by Si02 chromatography (EtOAc in hexanes, 5 to 15percent gradient) to afford the title compound (1.52 g, 69percent) as a white solid.
Reference: [1] Patent: WO2016/197078, 2016, A1, . Location in patent: Paragraph 626
[2] Gazzetta Chimica Italiana, 1964, vol. 94, p. 372 - 381
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