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Chemical Structure| 57933-83-2 Chemical Structure| 57933-83-2

Structure of 57933-83-2

Chemical Structure| 57933-83-2

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Product Details of [ 57933-83-2 ]

CAS No. :57933-83-2
Formula : C4H5ClO2
M.W : 120.53
SMILES Code : O=C(Cl)OC(C)=C
MDL No. :MFCD00037083

Safety of [ 57933-83-2 ]

Application In Synthesis of [ 57933-83-2 ]

* 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 [ 57933-83-2 ]

[ 57933-83-2 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 67-56-1 ]
  • [ 57933-83-2 ]
  • [ 1155-62-0 ]
  • [ 4652-65-7 ]
  • [ 5672-83-3 ]
  • 2
  • [ 57933-83-2 ]
  • [ 42835-25-6 ]
  • C18H16FNO5 [ No CAS ]
  • 3
  • [ 57933-83-2 ]
  • [ 145038-49-9 ]
  • 2-(9<i>H</i>-fluoren-9-ylmethoxycarbonylamino)-5-isopropenyloxycarbonyloxy-5-oxo-pentanoic acid methyl ester [ No CAS ]
  • 4
  • [ 3731-53-1 ]
  • [ 57933-83-2 ]
  • [ 42835-25-6 ]
  • [ 195191-84-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; EXAMPLE 3 9-fluoro-6,7-dihydro-5-methyl-N-[(4-pyridyl)methyl]-1-oxo-1H,5H-benzo-[i,j]quinolizine-2-carboxamide <strong>[42835-25-6]Flumequine</strong> (0.46 g) and dichloromethane (16.3 ml) were combined under nitrogen and cooled to 0 C. Triethylamine (0.27 ml) was then added dropwise, followed by isopropenylchloroformate (0.21 ml) and the whole stirred for 60 minutes. 4-(Aminomethyl)pyridine (0.2 ml) was then added and the reaction stirred for 20 h, after which time it was diluted with dichloromethane, washed with water (3 times), dried (MgSO4), concentrated in vacuo and triturated with acetone to give the title compound (0.49 g) as a yellow solid. TLC Rf =0.43 (10% MeOH/CH2 Cl2) m.p.=199-200 C.
  • 5
  • [ 13258-63-4 ]
  • [ 57933-83-2 ]
  • [ 42835-25-6 ]
  • 9-fluoro-6,7-dihydro-5-methyl-N-[2-(4-pyridyl)ethyl]-1-oxo-1H,5H-benzo-[i,j]quinolizine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; EXAMPLE 1 9-fluoro-6,7-dihydro-5-methyl-N-[2-(4-pyridyl)ethyl]-1-oxo-1H,5H-benzo-[i,j]quinolizine-2-carboxamide <strong>[42835-25-6]Flumequine</strong> (0.46 g) and dichloromethane (16.3 ml) were combined under nitrogen and cooled to 0 C. Triethylamnine (0.27 ml) was then added dropwise, followed by isopropenyl chloroformate (0.21 ml) and the whole stirred for 60 minutes. 4-(2-Aminoethyl)pyridine (0.23 ml) was then added and the reaction stirred for 20 h, concentrated onto silica and purified by flash column chromatography to give the title compound (0.55 g) as a white solid. TLC Rf =0.27 (5% MeOH/CH2 Cl2) mp=217 C.
  • 6
  • [ 57933-83-2 ]
  • [ 15910-91-5 ]
  • prop-1-en-2-yl (1-methylcyclopropanecarbonyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.9 g A -78 C. solution of <strong>[15910-91-5]1-methylcyclopropanecarboxamide</strong> (1.35 g, 13.6 mmol) in THF (30 mL) was treated drop-wise with lithium bis(trimethylsilyl)amide (1M THF, 17.7 mL, 17.7 mmol), stirred for 0.5 h, treated drop-wise with a solution of isopropenyl chloroformate (1.94 mL, 17.7 mmol) in THF (5 mL), stirred at -78 C. for 1 h, then allowed to warm to RT and stirred for 1 h. The mixture was quenched with satd. NaHCO3, extracted with EtOAc (3*) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford crude prop-1-en-2-yl (1-methylcyclopropanecarbonyl)carbamate (2.9 g, 116%) which was used without further purification.
A -78 C. solution of <strong>[15910-91-5]1-methylcyclopropanecarboxamide</strong> (1.35 g, 13.62 mmol) in THF (30 mL) was treated drop-wise with lithium bis(trimethylsilyl)amide (1 M THF, 17.7 mL, 17.7 mmol), stirred for 0.5 h, treated drop-wise with a solution of isopropenyl chloroformate (1.94 mL, 17.7 mmol) in THF (5 mL), stirred at -78 C. for 1 h, then allowed to warm to RT and stirred for 1 h. The mixture was quenched with satd. NaHCO3, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford crude prop-1-en-2-yl (1-methylcyclopropanecarbonyl)carbamate (2.9 g, 116%) which was used without further purification.
  • 7
  • [ 57933-83-2 ]
  • [ 33024-60-1 ]
  • prop-1-en-2-yl N-(tetrahydro-2H-pyran-4-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydrogencarbonate; In ethyl acetate; at 20℃; for 2h; A biphasic mixture of 4-aminotetrahydropyran hydrochloride (1.0 g, 7.27 mmol) in EtOAc (20 mL) and satd. NaHCO3 (20 mL) was treated with isopropenyl chloroformate (0.874 mL, 7.99 mmol), stirred at RT for 2 h and the layers separated. The aqueous layer was extracted with EtOAc (1*) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford prop-1-en-2-yl(tetrahydro-2H-pyran-4-yl)carbamate (1.2 g, 89percent). 1H NMR (400 MHz, DMSO-d6): delta 7.48 (d, J=7.7 Hz, 1H), 4.57 (d, J=7.9 Hz, 2H), 3.80-3.78 (m, 2H), 3.51-3.40 (m, 1H), 3.33-3.25 (m, 2H), 1.83 (s, 3H), 1.69 (m, 2H), 1.43-1.32 (m, 2H).
 

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