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[ CAS No. 39736-29-3 ]

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2D
Chemical Structure| 39736-29-3
Chemical Structure| 39736-29-3
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Product Details of [ 39736-29-3 ]

CAS No. :39736-29-3MDL No. :MFCD01830310
Formula :C7H10N2O2S2Boiling Point :368.6°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :218.30Pubchem ID :384908
Synonyms :

Computed Properties of [ 39736-29-3 ]

TPSA : 119 H-Bond Acceptor Count : 6
XLogP3 : 2.6 H-Bond Donor Count : 1
SP3 : 0.43 Rotatable Bond Count : 4

Safety of [ 39736-29-3 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 39736-29-3 ]

  • Upstream synthesis route of [ 39736-29-3 ]
  • Downstream synthetic route of [ 39736-29-3 ]

[ 39736-29-3 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 623-51-8 ]
  • [ 10191-60-3 ]
  • [ 39736-29-3 ]
YieldReaction ConditionsOperation in experiment
99% With diisopropylamine In N,N-dimethyl-formamide at 100℃; for 5.00 h; The synthesis of ethyl 4-amino-2-(methylthio)thiazole-5-carboxylate
Ethyl 2-mercaptoacetate (50 g, 0.416 mol) was dissolved in 500 ml of dimethylformamide and added with dimethyl N-thienodithioimino carbonate (67 g, 0.416 mol) and diisopropylamine (112 ml, 0.624 mol).
After heating at 100° C. for 5 hours, the mixture was extracted with 500 ml of saturated ammonium chloride and 500 ml of ethylacetate, dried with sodium sulfate, filtered and concentrated under vacuum.
After washing the solid with n-hexane, the title compound (90 g, 99percent) was obtained.
1H-NMR (400 MHz, CDCl3); δ 5.84 (brs, 2H), 4.26 (q, J=7.2 Hz, 2H), 2.63 (s, 3H), 1.32 (t, J=7.2 Hz, 3H); LC-MS 219 (MH+)
89% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; Ethyl 2-mercaptoacetate (5 g, 42 mmol, 1.0 eq) was dissolved in DMF (50 mL) and added with N-thienodi-thioimino carbonate (6.1 g, 42 mmol, 1.0 eq) and DIPEA (16.3 g, 126 mmol, 3.0 eq). After heating at 100 °C for 5 h, the mixture was diluted with saturated aqueous ammonium chloride (100 mL) and extracted with EtOAc (100 mLx2). The combined organic layer was washed with brine, dried, concentrated. The solid was washed with n-hexane and dried under vacuum to give the title compound (8 g, yield: 89percent) as a yellow solid. ESI-MS (M+H)+: 219.0.
Reference: [1] Patent: US2013/72482, 2013, A1. Location in patent: Paragraph 0315-0317
[2] Patent: WO2015/89327, 2015, A1. Location in patent: Paragraph 0468
[3] Tetrahedron Letters, 1966, # 17, p. 1885 - 1889
[4] Patent: WO2015/193506, 2015, A1. Location in patent: Page/Page column 57-58
  • 2
  • [ 10191-61-4 ]
  • [ 105-36-2 ]
  • [ 39736-29-3 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: for 1.00 h; Reflux
Stage #2: With triethylamine In ethanol for 4.00 h; Reflux
The ethyl bromoacetate (1.96 g, 11.76 mmol) was added to a stirred solution of potassium methyl cyanimidodithiocarbonate 1 (2.0 g, 11.76 mmol) in EtOH (50 mL). The mixture was heated to reflux for 1 h. After cooling, Et3N (2.38 g, 23.52 mmol) was added and the mixture was heated to reflux for 4 h. The ethanol was evaporated and the residue was triturated with water (20 mL) followed by filtering. The solid was dried and then recrystallized from acetone to give compound 2 (2.4 g, 93percent). Light yellow solid; mp 101-103 °C; 1H NMR (400 MHz, CDCl3) δ (ppm): 5.80 (brs, 2H), 4.26 (q, 2H, J = 7.2 Hz), 2.63 (s, 3H), 1.32 (t, 3H, J = 7.2 Hz); HRMS (ESI) Calcd. for C7H11N2O2S2 [M+H]+: 219.0256; Found: 219.0248.
Reference: [1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 22, p. 5911 - 5920
[2] Patent: WO2011/100838, 2011, A1. Location in patent: Page/Page column 60; 61
  • 3
  • [ 623-51-8 ]
  • [ 39736-29-3 ]
Reference: [1] Patent: US5326776, 1994, A
  • 4
  • [ 84911-18-2 ]
  • [ 10191-61-4 ]
  • [ 39736-29-3 ]
YieldReaction ConditionsOperation in experiment
155 mg at 20℃; for 0.33 h; Green chemistry General procedure: To asolution of acyclic 1,3-dicarbonyl compounds 12 (1.0 mmol) in EtOH (3.0 mL) was added NBS (178 mg, 1 mmol). Thereaction mixture was stirred for 10 min (30 min for 12b and 12e) at roomtemperature. Afterwards 7 (1 mmol)was added and the reaction mixture was stirred for another 20 min at roomtemperature. After that, the solvent was evaporated under reducedpressure, and the residue was purified viaa short silica gel column to afford the desired product 11.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 1, p. 259 - 263
  • 5
  • [ 55919-47-6 ]
  • [ 10191-61-4 ]
  • [ 39736-29-3 ]
YieldReaction ConditionsOperation in experiment
138 mg at 20℃; for 0.33 h; Green chemistry General procedure: To asolution of acyclic 1,3-dicarbonyl compounds 12 (1.0 mmol) in EtOH (3.0 mL) was added NBS (178 mg, 1 mmol). Thereaction mixture was stirred for 10 min (30 min for 12b and 12e) at roomtemperature. Afterwards 7 (1 mmol)was added and the reaction mixture was stirred for another 20 min at roomtemperature. After that, the solvent was evaporated under reducedpressure, and the residue was purified viaa short silica gel column to afford the desired product 11.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 1, p. 259 - 263
  • 6
  • [ 105-39-5 ]
  • [ 39736-29-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2008, vol. 45, # 4, p. 1071 - 1076
  • 7
  • [ 10191-61-4 ]
  • [ 105-39-5 ]
  • [ 39736-29-3 ]
Reference: [1] Tetrahedron, 1976, vol. 32, p. 623 - 627
[2] Justus Liebigs Annalen der Chemie, 1972, vol. 764, p. 125 - 130
  • 8
  • [ 10191-67-0 ]
  • [ 39736-29-3 ]
Reference: [1] European Journal of Medicinal Chemistry, 2013, vol. 63, p. 213 - 223
  • 9
  • [ 10191-61-4 ]
  • [ 105-36-2 ]
  • [ 39736-29-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, # 5, p. 1361 - 1366
  • 10
  • [ 623-51-8 ]
  • [ 10191-60-3 ]
  • [ 39736-29-3 ]
YieldReaction ConditionsOperation in experiment
99% With diisopropylamine In N,N-dimethyl-formamide at 100℃; for 5.00 h; The synthesis of ethyl 4-amino-2-(methylthio)thiazole-5-carboxylate
Ethyl 2-mercaptoacetate (50 g, 0.416 mol) was dissolved in 500 ml of dimethylformamide and added with dimethyl N-thienodithioimino carbonate (67 g, 0.416 mol) and diisopropylamine (112 ml, 0.624 mol).
After heating at 100° C. for 5 hours, the mixture was extracted with 500 ml of saturated ammonium chloride and 500 ml of ethylacetate, dried with sodium sulfate, filtered and concentrated under vacuum.
After washing the solid with n-hexane, the title compound (90 g, 99percent) was obtained.
1H-NMR (400 MHz, CDCl3); δ 5.84 (brs, 2H), 4.26 (q, J=7.2 Hz, 2H), 2.63 (s, 3H), 1.32 (t, J=7.2 Hz, 3H); LC-MS 219 (MH+)
89% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; Ethyl 2-mercaptoacetate (5 g, 42 mmol, 1.0 eq) was dissolved in DMF (50 mL) and added with N-thienodi-thioimino carbonate (6.1 g, 42 mmol, 1.0 eq) and DIPEA (16.3 g, 126 mmol, 3.0 eq). After heating at 100 °C for 5 h, the mixture was diluted with saturated aqueous ammonium chloride (100 mL) and extracted with EtOAc (100 mLx2). The combined organic layer was washed with brine, dried, concentrated. The solid was washed with n-hexane and dried under vacuum to give the title compound (8 g, yield: 89percent) as a yellow solid. ESI-MS (M+H)+: 219.0.
Reference: [1] Patent: US2013/72482, 2013, A1. Location in patent: Paragraph 0315-0317
[2] Patent: WO2015/89327, 2015, A1. Location in patent: Paragraph 0468
[3] Tetrahedron Letters, 1966, # 17, p. 1885 - 1889
[4] Patent: WO2015/193506, 2015, A1. Location in patent: Page/Page column 57-58
  • 11
  • [ 10191-61-4 ]
  • [ 105-36-2 ]
  • [ 39736-29-3 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: for 1.00 h; Reflux
Stage #2: With triethylamine In ethanol for 4.00 h; Reflux
The ethyl bromoacetate (1.96 g, 11.76 mmol) was added to a stirred solution of potassium methyl cyanimidodithiocarbonate 1 (2.0 g, 11.76 mmol) in EtOH (50 mL). The mixture was heated to reflux for 1 h. After cooling, Et3N (2.38 g, 23.52 mmol) was added and the mixture was heated to reflux for 4 h. The ethanol was evaporated and the residue was triturated with water (20 mL) followed by filtering. The solid was dried and then recrystallized from acetone to give compound 2 (2.4 g, 93percent). Light yellow solid; mp 101-103 °C; 1H NMR (400 MHz, CDCl3) δ (ppm): 5.80 (brs, 2H), 4.26 (q, 2H, J = 7.2 Hz), 2.63 (s, 3H), 1.32 (t, 3H, J = 7.2 Hz); HRMS (ESI) Calcd. for C7H11N2O2S2 [M+H]+: 219.0256; Found: 219.0248.
Reference: [1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 22, p. 5911 - 5920
[2] Patent: WO2011/100838, 2011, A1. Location in patent: Page/Page column 60; 61
  • 12
  • [ 623-51-8 ]
  • [ 39736-29-3 ]
Reference: [1] Patent: US5326776, 1994, A
  • 13
  • [ 84911-18-2 ]
  • [ 10191-61-4 ]
  • [ 39736-29-3 ]
YieldReaction ConditionsOperation in experiment
155 mg at 20℃; for 0.33 h; Green chemistry General procedure: To asolution of acyclic 1,3-dicarbonyl compounds 12 (1.0 mmol) in EtOH (3.0 mL) was added NBS (178 mg, 1 mmol). Thereaction mixture was stirred for 10 min (30 min for 12b and 12e) at roomtemperature. Afterwards 7 (1 mmol)was added and the reaction mixture was stirred for another 20 min at roomtemperature. After that, the solvent was evaporated under reducedpressure, and the residue was purified viaa short silica gel column to afford the desired product 11.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 1, p. 259 - 263
  • 14
  • [ 55919-47-6 ]
  • [ 10191-61-4 ]
  • [ 39736-29-3 ]
YieldReaction ConditionsOperation in experiment
138 mg at 20℃; for 0.33 h; Green chemistry General procedure: To asolution of acyclic 1,3-dicarbonyl compounds 12 (1.0 mmol) in EtOH (3.0 mL) was added NBS (178 mg, 1 mmol). Thereaction mixture was stirred for 10 min (30 min for 12b and 12e) at roomtemperature. Afterwards 7 (1 mmol)was added and the reaction mixture was stirred for another 20 min at roomtemperature. After that, the solvent was evaporated under reducedpressure, and the residue was purified viaa short silica gel column to afford the desired product 11.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 1, p. 259 - 263
  • 15
  • [ 105-39-5 ]
  • [ 39736-29-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2008, vol. 45, # 4, p. 1071 - 1076
  • 16
  • [ 10191-61-4 ]
  • [ 105-39-5 ]
  • [ 39736-29-3 ]
Reference: [1] Tetrahedron, 1976, vol. 32, p. 623 - 627
[2] Justus Liebigs Annalen der Chemie, 1972, vol. 764, p. 125 - 130
  • 17
  • [ 10191-67-0 ]
  • [ 39736-29-3 ]
Reference: [1] European Journal of Medicinal Chemistry, 2013, vol. 63, p. 213 - 223
  • 18
  • [ 10191-61-4 ]
  • [ 105-36-2 ]
  • [ 39736-29-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, # 5, p. 1361 - 1366
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