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Chemical Structure| 16982-21-1 Chemical Structure| 16982-21-1
Chemical Structure| 16982-21-1

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CAS No.: 16982-21-1

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Product Details of 2-Thiooxamic acid ethyl ester

CAS No. :16982-21-1
Formula : C4H7NO2S
M.W : 133.17
SMILES Code : O=C(OCC)C(N)=S
MDL No. :MFCD00074903
InChI Key :YMBMCMOZIGSBOA-UHFFFAOYSA-N
Pubchem ID :2733398

Safety of 2-Thiooxamic acid ethyl ester

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 2-Thiooxamic acid ethyl ester

* 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.

  • Upstream synthesis route of [ 16982-21-1 ]
  • Downstream synthetic route of [ 16982-21-1 ]

[ 16982-21-1 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 16982-21-1 ]
  • [ 69267-75-0 ]
  • [ 439692-05-4 ]
YieldReaction ConditionsOperation in experiment
98% for 1 h; Reflux A solution of 2-bromo-1-cyclopropyl-ethanone (intermediate 12) (6.80 g, 42.0 mmol) and amino-thioxo-acetic acid ethyl ester (intermediate 6) (4.66 g, 35.0 mmol) in ethanol (50 mL) was heated to reflux for 1 hour. The reaction mixture was concentrated to dryness. The residue was purified by the flash column chromatography (silica, hexanes/ethyl acetate=4:1) to afford the title compound (6.7 g, 98percent).MS calcd for (C9H11NO2S+H)+: 198.06MS found: (M+H)+=198.05
References: [1] Patent: US2010/196321, 2010, A1, . Location in patent: Page/Page column 22.
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7351 - 7356.
  • 2
  • [ 16982-21-1 ]
  • [ 188869-05-8 ]
  • [ 1053656-51-1 ]
YieldReaction ConditionsOperation in experiment
60% With sodium hydrogencarbonate In isopropyl alcohol for 12 h; Reflux Compound 18 9 (4.0g, 14.4mmol) was dissolved in IPA (25mL). 20 Ethyl thioxamate (1.60g, 12.0mmol) and 146 NaHCO3 (2.01g, 24.0mmol) were added. The mixture was refluxed for 12h, followed by concentration. The residue was taken in 63 water and extracted with dichloromethane. The organic layer was washed with water, brine and dried over anhydrous Na2SO4 and concentrated to the desired compound (2.2g, 60percent), which is pure enough for the next step. mp: 138–140°C; 1H NMR (300MHz, CDCl3): δ 4.71(s, 2H), 4.48(q, J=12Hz, 2H,), 3.72(m, 2H), 2.96(t, J=5.4Hz, 2H), 2.41(t, J=6.3Hz, 2H), 1,51(s, 9H), 1,44(t, J=1.2Hz, 3H,); MS (ESI) m/z: 335.1 [M+Na]+.
References: [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 23-24, p. 5987 - 5999.
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 2, p. 443 - 454.
 

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