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[ CAS No. 67808-33-7 ]

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2D
Chemical Structure| 67808-33-7
Chemical Structure| 67808-33-7
Structure of 67808-33-7 *Storage: {[proInfo.prStorage]}

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Alternatived Products of [ 67808-33-7 ]

Product Details of [ 67808-33-7 ]

CAS No. :67808-33-7MDL No. :MFCD05664843
Formula : C7H5NO2S Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :167.19Pubchem ID :-
Synonyms :

Computed Properties of [ 67808-33-7 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 67808-33-7 ]

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Application In Synthesis of [ 67808-33-7 ]

  • Downstream synthetic route of [ 67808-33-7 ]

[ 67808-33-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 62224-16-2 ]
  • [ 544-92-3 ]
  • [ 67808-33-7 ]
  • 3
  • [ 62224-16-2 ]
  • copper(l) cyanide [ No CAS ]
  • [ 67808-33-7 ]
YieldReaction ConditionsOperation in experiment
56.8% With potassium iodide; In N,N-dimethyl-formamide; at 190℃; for 4h; Add M-72.21g (10mmol), cuprous cyanide 5.3g (30mmol), potassium iodide 0.16g (1mmol) in 60ml anhydrous DMF6ml pressure tube. Heating under inert gas protection conditions to 190 C, 4h after TLC showed the starting material is no longer remaining. The reaction was poured into a mixture of ice and aqueous ammonia, extracted with ethyl acetate (20ml × 3), the combined organic phase was washed twice with saturated brine, dried over anhydrous MgSO 4, and concentrated under reduced pressure column chromatography (PE: EA = 80:1), as a white solid 0.95g, yield 56.8%.
56.8% With potassium iodide; In N,N-dimethyl-formamide; at 180℃; for 4h;Sealed tube; Inert atmosphere; A dry sealed tube was charged of <strong>[62224-16-2]methyl 4-bromothiophene-2-carboxylate</strong> (2.21 g,10 mmol), CuCN (5.3 g, 30 mmol), KI (0.16 g, 1 mmol) and anhydrous DMF (6 mL) under argon atmosphere. The reaction mixture was stirred for 4 h at 180 C, and then allowed to cool to room temperature. The reaction solution was poured into the mixture of ice and aqua ammonia and extracted with ethyl acetate(20 mL 3). The combined organic layers were washed with saturated brine twice and dried with anhydrous MgSO4, followed by concentration in vacuo. The crude compound was purified by silicagel column chromatography (hexane/ethyl acetate, 80:1) to yield the title compound as a white solid (0.95 g, 56.8%). 1H NMR(300 MHz CDCl3) d: 8.09 (s, 1H), 7.93 (s, 1H), 3.93 (s, 3H). 13C NMR(126 MHz CDCl3) d: 156.17, 135.71, 131.07, 129.33, 109.28, 106.72,48.08. MS (ESI, m/z): 168.1 [MH], 166.2 [MH]-.
With potassium iodide; In N,N-dimethyl-formamide; at 160℃; for 10h;Sealed tube; Inert atmosphere; In a sealed tube, compound 1 (5.00g, 22.6mmol) was dissolved in anhydrous DMF (5mL) followed by the addition of cuprous cyanide (6.08g, 67.9mmol) and potassium iodide (0.01g, 0.06mmol) under an argon atmosphere. Reaction mixture was heated at 160C for 10h. After this period, the reaction was quenched with a mixed solution of ammonia and ice water (v/v=1 : 3, 50mL). The precipitate was filtered out and rinsed with ethyl acetate. The filtrate was' extracted with ethyl acetate (40mL×3). The combined organic phase was washed twice with saturated brine (30mL×2) and dried over anhydrous MgSO4. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography (PE : EA=20 : 1) to give title compound as a white solid. Yield: 79%; mp: 107-109C. 1H NMR (300MHz, CDCl3) delta: 8.09 (s, 1H), 7.93 (s, 1H), 3.93 (s, 3H). MS (m/z): [M+H]+ 168.1.
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