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[ CAS No. 53174-98-4 ]

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Chemical Structure| 53174-98-4
Chemical Structure| 53174-98-4
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CAS No. :53174-98-4 MDL No. :MFCD07772791
Formula : C8H5NOS Boiling Point : 320.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :163.20 g/mol Pubchem ID :289925
Synonyms :

Safety of [ 53174-98-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 53174-98-4 ]

  • Upstream synthesis route of [ 53174-98-4 ]
  • Downstream synthetic route of [ 53174-98-4 ]

[ 53174-98-4 ] Synthesis Path-Upstream   1~4

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YieldReaction ConditionsOperation in experiment
66%
Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at 20℃; for 19 h; Inert atmosphere; Cooling with ethanol-dry ice
Stage #2: for 1 h; Cooling with ice; Inert atmosphere
Thieno[2,3-b]pyridine-2-carbaldehyde: In an atmosphere of argon a mixture of 1.3 mL (2.08 mmol) of 0.8 M n-butyllithium in hexane and 0.3 mL (3.3 mmol) of N,N,N’,N’-tetramethylethylenediamine was stirred magnetically at room temperature for 30 minutes, diluted with 5 mL of hexane, cooled in a bath of dry ice-ethanol, and treated (with vigorous stirring) dropwise (from a syringe with a small needle) with 0.23 g (1.7 mmol) of thieno[2,3-b] pyridine. The mixture was stirred in the bath for 7 h longer and then for 12 h while it warmed to room temperature. It was cooled in ice, treated with 0.15 g (2.1 mmol) of dimethylformamide, stirred for one hour, and then treated successively with 1 mL of ethanol, 3 mL of saturated aqueous ammonium chloride solution, and 4 mL of water. The layers were separated. The organic layer (plus chloroform extracts of the aqueous layer) was dried (magnesium sulfate) and evaporated. The residue was triturated with hexane to give 0.18 g (66percent) of brown solid; m.p. 131.5-132.5 °C. Recrystallizations from ethanol (once with charcoal) gave white needles. 1H NMR (300 MHz, CDCl3) ppm 7.41 (dd, J = 4.5 Hz, 8.1 Hz, 1 H), 7.99 (s, 1 H), 8.24 (dd, J = 1.8 Hz, 8.1 Hz, 1 H), 8.73 (dd, J = 1.8 Hz, 4.5 Hz, 1 H), 10.12 (s, 1 H). 13C NMR (75 MHz, CDCl3) ppm 120.7, 131.8, 132.3, 134.0, 143.2, 150.5, 163.8, 185.0. IR (CHCl3, cm-1) 1682 (C=O). MS (EI, 70 eV): m/z [percent] = 162[M]+ (100), 134[M-CO]+ (26). HRMS (FAB+) calculated for C8H6NOS [M+1] 164.0170, found 164.0167.
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 20, p. 1952 - 1956
[2] Tetrahedron Letters, 1994, vol. 35, # 7, p. 1011 - 1014
[3] Journal of Heterocyclic Chemistry, 1974, vol. 11, p. 355 - 361
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YieldReaction ConditionsOperation in experiment
85% With manganese(IV) oxide In dichloromethane at 20℃; To a solution of compound B-131 (4.0 g, 24 mmol) in dichloromethane (40 mL) was added manganese dioxide (21 g, 24 mmol) at room temperature. The mixture was stirred at room temperature overnight. On completion, the mixture was filtered, and the filtrate was concentrated in vacuo to give compound B-132 (3.4 g, 85percent yield) as a yellow solid. LCMS: (ES+) m/z (M+H)+ = 164.1, tR=0.537.
Reference: [1] Patent: WO2015/66371, 2015, A1, . Location in patent: Paragraph 00264-00265
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Reference: [1] Patent: WO2015/66371, 2015, A1,
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Reference: [1] Patent: WO2015/66371, 2015, A1,
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