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Chemical Structure| 203661-13-6 Chemical Structure| 203661-13-6

Structure of 203661-13-6

Chemical Structure| 203661-13-6

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Product Details of [ 203661-13-6 ]

CAS No. :203661-13-6
Formula : C7H8N2O2S
M.W : 184.22
SMILES Code : O=C(C(C=C1N)=CNC1=S)OC

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Application In Synthesis of [ 203661-13-6 ]

* 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 [ 203661-13-6 ]

[ 203661-13-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 59237-53-5 ]
  • [ 203661-13-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium hydrogensulfide; In methanol; di-isopropyl ether; Production Example 105 Methyl 5-amino-6-mercaptonicotinate To a solution of 6 g of <strong>[59237-53-5]methyl 6-chloro-5-nitronicotinate</strong> in methanol (100 ml) was added 6.7 g of sodium hydrogensulfide and the resulting mixture was heated under reflux for 2 hours. After distilling off the solvent under reduced pressure, dilute hydrochloric acid was added to the residue followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. Diisopropyl ether was added to the residue and the crystals thus precipitated were taken up by filtration to thereby give 24.7 g of the title compound as yellow crystals. 1H-NMR(DMSO-d6) delta ppm: 3.78(s, 3H),5.91-6.00(br.s, 2H), 7.12(d, J=2.0 Hz, 1H), 7.53(dd, J=2.0, 6.4 Hz, 1H)
  • 2
  • [ 59237-53-5 ]
  • [ 203661-13-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium sulfide nonahydrate; hydrogen sulfide; sodium acetate; sodium sulfate; zinc; In 1,4-dioxane; methanol; water; acetic acid; (a) 5-Amino-6-thioxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester A mixture of sodium sulfide nonahydrate (2.17 g) and sulfur (0.29 g) was heated in boiling water (20 ml) until the solution was homogeneous and added to a solution of 6-chloro-5-nitro-nicotinic acid methyl ester [prepared as described by A. H. Berrie et al. J. Chem. Soc. 2590-2594 (1951)] (3.10 g) in methanol (50 ml). The mixture was boiled for 15 minutes and cooled. The resulting disulfide was collected and washed with water to give a yellow solid (2.46 g). The solid (5 g) in acetic acid (100 ml) and 4M HCl in dioxan (50 ml) was treated with zinc dust (12 g) and the mixture was stirred at room temperature for 30 minutes, filtered and evaporated to dryness. Sodium acetate and sodium sulfate were added and the mixture was extracted with warm chloroform and chromatographed on silica gel, eluding with chloroform then methanol-chloroform to afford a yellow solid (2.3 g). MS (+ve ion electrospray) m/z 185(MH+)
 

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