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Chemical Structure| 60838-50-8 Chemical Structure| 60838-50-8

Structure of 60838-50-8

Chemical Structure| 60838-50-8

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Product Details of [ 60838-50-8 ]

CAS No. :60838-50-8
Formula : C4H5NO
M.W : 83.09
SMILES Code : N#C/C=C/OC
MDL No. :MFCD00044798
InChI Key :IPCRTSDORDQHRO-DUXPYHPUSA-N
Pubchem ID :5324713

Safety of [ 60838-50-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H315-H319-H332-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 60838-50-8 ]

* 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.

  • Downstream synthetic route of [ 60838-50-8 ]

[ 60838-50-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 60838-50-8 ]
  • [ 100-63-0 ]
  • [ 1128-56-9 ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate; In tert-butyl alcohol; at 20℃; for 15h; To a hot solution of tert-BuOK (100 g, Tokyo Kasei) in TERT-BUOH (650 mL) was added phenylhydrazine 3-3 (39.36 mL, Tokyo Kasei). After cooling to ambient temperature, methoxyacrylonitrile 3-4 (33.57 mL, Tokyo Kasei) was added dropwise and the mixture was refluxed for 15 hours. The reaction mixture was cooled to ambient temperature and the solvent was removed by evaporation. To the residue was added water (200 mL) and EtOAc (500 mL). The layers were separated and the organic layer was washed with brine (200 mL), dried over MGS04 and concentrated. To the residue was added 5N HC1 (200 mL) and EtOAc (500 mL) and the precipitated solids were removed by filtration. The filtered layers were separated, and the organic layer was EXTRACTED WITH 5N HC1 (100 ML). THE AQUEOUS LAYERS WERE combined and treated with 5N NaOH to adjust the solution to a pH of about 9, then the aqueous solution was extracted with EtOAc (400 mL + 200 mL). The organic layers were combined and washed with brine (100 mL), dried over MGS04 and concentrated. The resulting residue was purified by flash chromatography on silica gel (Wako gel C-300, Wako, EtOAc/hexane 1: 9 to 1: 1) to give compound 3-2. 1H NMR (300 MHz, DMSO-d6): 8 8.11 (d, J=2.6 Hz, 1H), 7.62 (dd, J=8.7, 1. 1 HZ, 2H), 7.37 (dd, J=8.7, 7. 4 Hz, 2H), 7.10 (dt, J=7.4, 1.1 Hz, 1H), 5.72 (d, J=2.6 Hz, 1H), 5. 01 (brs, 2H).
  • 2
  • [ 60838-50-8 ]
  • [ 7803-49-8 ]
  • [ 14678-05-8 ]
YieldReaction ConditionsOperation in experiment
In water; at 80℃; for 3.0h; The 5-aminoisoxazole used as starting material was prepared as follows:- EPO <DP n="53"/>A 50% w/w solution of hydroxylaminbeta in water (6.6 m) and3-methoxyacrylonitrile (8.39 ml) were heated at 8O0C for 3 hours. The reaction mixture was cooled to room temperature and extracted with diethyl ether. The combined organic layers were washed with brine, dried (magnesium sulphate) and concentrated to a brown oil which solidifed on standing to give the title compound (3.87 g); NMR Spectrum: (DMSOd6) 4.88 (d, IH), 6.60 (s, 2H), 7.97 (d, IH); Mass Spectrum: M+ 83.
  • 3
  • [ 60838-50-8 ]
  • [ 59-88-1 ]
  • [ 1128-56-9 ]
YieldReaction ConditionsOperation in experiment
85% With sodium ethanolate; In ethanol; at 150℃; for 2h;Sealed tube; Microwave irradiation; 3.6 3-Amino-1-phenyl-1H-pyrazole (11a) A solution of phenylhydrazine hydrochloride (2d·HCl) (0.17 g, 1.2 mmol), 3-methoxyacrylonitrile (1a) (0.20 mL, 2.4 mmol) and NaOEt (0.41 g, 4.8 mmol) in dry EtOH (4 mL) was irradiated at 150 C for 2 h in a sealed, pressure-rated Pyrex tube (10 mL) using a CEM Discover microwave synthesizer by moderating the initial power (150 W). The mixture was cooled by passing a stream of compressed air through the microwave cavity and H2O was added (10 mL). The aqueous layer was extracted with EtOAc (2*20 mL) and the organic extracts were combined, washed with brine, dried (MgSO4) and evaporated in vacuo. Purification by column chromatography on silica, eluting with hexane/EtOAc (1:3 v/v), gave the title compound (0.19 g, 85%) as a yellow solid, mp 90-92 C (lit. 44 mp 91 C) (found: 159.0796. C9H9N3 [M] requires 159.0796); FTIR (KBr)/cm-1 numax 3477 (NH), 3297 (NH), 1490, 1415, 1367, 1172; 1H NMR (400 MHz; DMSO-d6) delta 8.13 (1H, d, J 2.4, H-5), 7.64 (2H, d, J 7.7, H-2'/H-6'), 7.39 (2H, t, J 7.7, H-3'/H-5'), 7.11 (1H, t, J 7.7, H-4'), 5.74 (1H, d, J 2.4, H-4), 5.09 (2H, br s, exch. D2O, NH2); 13C NMR (126 MHz; DMSO-d6) delta 157.5 (C), 140.4 (C), 129.7 (CH), 128.2 (CH), 124.3 (CH), 116.8 (CH), 96.8 (CH); LRMS (EI) m/z (rel intensity) 159 (M<ce:glyph name="rad"/>+, 100), 158 ([M-1]+, 30), 131 ([M-N2]<ce:glyph name="rad"/>+, 13), 104 (16), 92 (8), 84 (27), 77 (Ph+, 29).
  • 4
  • [ 60838-50-8 ]
  • [ 51285-26-8 ]
  • [ 61310-37-0 ]
YieldReaction ConditionsOperation in experiment
73% A mixture of 157.8 g. (1.0 mol) of 2-pyridinecarboxamidine hydrochloride 23, 54.2 g (1.0 mol) of sodium methoxide in 400 ml of dry methanol was stirred for 30 minutes. The sodium chloride was filtered and the filtrate was concentrated to dryness. The residue and 83 g (1.0 mole) of 3-methoxyacrylonitrile 24 were heated (100-160°) together for 3 hours, at this point the evolution of ethanol had stopped and the melt had started to crystallize. The product 25 was cooled to room temperature, suspended in methanol, filtered and dried to obtain 25 125.6 g, (73percent yield).
 

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