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Chemical Structure| 80-73-9
Chemical Structure| 80-73-9
Structure of 80-73-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 80-73-9 ]

CAS No. :80-73-9 MDL No. :MFCD00003188
Formula : C5H10N2O Boiling Point : -
Linear Structure Formula :- InChI Key :CYSGHNMQYZDMIA-UHFFFAOYSA-N
M.W : 114.15 Pubchem ID :6661
Synonyms :

Calculated chemistry of [ 80-73-9 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.25
TPSA : 23.55 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.51
Log Po/w (XLOGP3) : -0.49
Log Po/w (WLOGP) : -0.78
Log Po/w (MLOGP) : 0.03
Log Po/w (SILICOS-IT) : -0.19
Consensus Log Po/w : 0.01

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.24
Solubility : 65.8 mg/ml ; 0.577 mol/l
Class : Very soluble
Log S (Ali) : 0.46
Solubility : 331.0 mg/ml ; 2.9 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.01
Solubility : 117.0 mg/ml ; 1.03 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.34

Safety of [ 80-73-9 ]

Signal Word:Danger Class:N/A
Precautionary Statements:P201-P202-P264-P270-P273-P280-P301+P312+P330-P305+P351+P338+P310-P308+P313-P405-P501 UN#:N/A
Hazard Statements:H302-H318-H361-H402 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 80-73-9 ]

* 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 [ 80-73-9 ]
  • Downstream synthetic route of [ 80-73-9 ]

[ 80-73-9 ] Synthesis Path-Upstream   1~68

  • 1
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Reference: [1] Synthesis, 2010, # 24, p. 4251 - 4255
[2] Organic Letters, 1999, vol. 1, # 7, p. 961 - 964
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Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 31, p. 7705 - 7706
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YieldReaction ConditionsOperation in experiment
63% With sodium formate; potassium carbonate In formic acid EXAMPLE 4
320 g (2.2 mol) 1,3-bis(hydroxymethyl)-imidazolidin-2-one and 200 g (2.9 mol) sodium formate were dissolved in 620 g (13.5 mol) formic acid and heated 8 hr at reflux.
Then 238 g formic acid was distilled off under reduced pressure, and 200 g potassium carbonate was added port:onwise to the residue.
After cooling, the raw product was decanted from the salts which had precipitated, was washed with a small amount of methylene chloride, and was distilled in vacuum.
157 g 1,3-dimethyl-imidazolidin-2-one was obtained at 90°-95° C. and 3 torr. Yield=63percent. Purity>98percent by GC and 1 H-NMR.
Reference: [1] Patent: US4864026, 1989, A,
  • 4
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Reference: [1] Journal of the American Chemical Society, 1981, vol. 103, p. 4837
[2] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2010, vol. 65, # 7, p. 861 - 872
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Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 31, p. 7705 - 7706
  • 6
  • [ 120-93-4 ]
  • [ 50-00-0 ]
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Reference: [1] Patent: US4864026, 1989, A,
[2] Patent: CN107954935, 2018, A, . Location in patent: Paragraph 0021-0022; 0025-0026; 0027-0028
  • 7
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Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 31, p. 7705 - 7706
  • 8
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Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 31, p. 7705 - 7706
  • 9
  • [ 143-07-7 ]
  • [ 37091-73-9 ]
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Reference: [1] Patent: US5750779, 1998, A,
  • 10
  • [ 1205534-16-2 ]
  • [ 93-91-4 ]
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  • [ 2009-96-3 ]
Reference: [1] Synlett, 2009, # 18, p. 2943 - 2944
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 25, p. 4397 - 4406
  • 11
  • [ 124-38-9 ]
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Reference: [1] Green Chemistry, 2013, vol. 15, # 6, p. 1567 - 1577
[2] Journal of Organic Chemistry, 1992, vol. 57, # 28, p. 7339 - 7342
[3] Chemical Communications, 2009, # 3, p. 349 - 351
  • 12
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Reference: [1] Journal of the American Chemical Society, 1981, vol. 103, p. 4837
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Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 28, p. 7339 - 7342
  • 14
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Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 31, p. 7705 - 7706
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Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 31, p. 7705 - 7706
  • 16
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  • [ 286-20-4 ]
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Reference: [1] Helvetica Chimica Acta, 2005, vol. 88, # 12, p. 3253 - 3262
  • 17
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Reference: [1] Synthetic Communications, 1988, vol. 18, # 5, p. 487 - 494
  • 18
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  • [ 110-70-3 ]
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Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 28, p. 7339 - 7342
  • 19
  • [ 13461-16-0 ]
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Reference: [1] Helvetica Chimica Acta, 2005, vol. 88, # 12, p. 3253 - 3262
  • 20
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Reference: [1] Synthetic Communications, 1984, vol. 14, # 11, p. 1073 - 1080
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Reference: [1] Synthetic Communications, 1984, vol. 14, # 11, p. 1073 - 1080
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Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 31, p. 7705 - 7706
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Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 31, p. 7705 - 7706
  • 24
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Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 31, p. 7705 - 7706
  • 25
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Reference: [1] Patent: US5583256, 1996, A,
  • 26
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Reference: [1] Patent: US5783706, 1998, A,
  • 27
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Reference: [1] Journal of Organometallic Chemistry, 1991, vol. 419, # 1, p. 9 - 26
  • 28
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Reference: [1] Synthetic Communications, 1984, vol. 14, # 11, p. 1073 - 1080
  • 29
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Reference: [1] Synthesis, 1982, # 6, p. 464 - 465
[2] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 1, p. 89 - 95[3] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 1, p. 101 - 108
  • 30
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Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 1, p. 97 - 101
  • 31
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Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 1, p. 97 - 101
  • 32
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Reference: [1] Patent: US2422400, 1944, ,
  • 33
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Reference: [1] Synthesis, 1983, # 12, p. 1032 - 1033
  • 34
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  • [ 80767-12-0 ]
Reference: [1] Macromolecules, 2013, vol. 46, # 13, p. 5157 - 5166
  • 35
  • [ 96-09-3 ]
  • [ 25653-11-6 ]
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Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 24, p. 8504 - 8505
  • 36
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Reference: [1] Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 1983, vol. 39, # 10, p. 929 - 932
  • 37
  • [ 75-44-5 ]
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Reference: [1] Journal of Molecular Structure, 1981, vol. 77, p. 239 - 252
  • 38
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Reference: [1] Journal of Medicinal Chemistry, 1981, vol. 24, # 9, p. 1089 - 1092
  • 39
  • [ 68696-80-0 ]
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  • [ 36107-45-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1981, p. 317 - 319
  • 40
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  • [ 1012-34-6 ]
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Reference: [1] Journal of Organometallic Chemistry, 1991, vol. 419, # 1, p. 9 - 26
  • 41
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Reference: [1] Macromolecules, 2013, vol. 46, # 13, p. 5157 - 5166
  • 42
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Reference: [1] Macromolecules, 2013, vol. 46, # 13, p. 5157 - 5166
  • 43
  • [ 75-44-5 ]
  • [ 110-70-3 ]
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  • [ 117688-91-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1989, vol. 32, # 1, p. 228 - 236
  • 44
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Reference: [1] Organic Letters, 2008, vol. 10, # 8, p. 1517 - 1520
  • 45
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  • [ 31603-49-3 ]
Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 11, p. 3928 - 3939
  • 46
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Reference: [1] Chemistry Letters, 2001, # 8, p. 758 - 759
  • 47
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  • [ 26184-65-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 46, p. 11531 - 11534[2] Angew. Chem., 2012, vol. 124, # 46, p. 11699 - 11702,4
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Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 11, p. 3928 - 3939
  • 49
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Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 46, p. 11531 - 11534[2] Angew. Chem., 2012, vol. 124, # 46, p. 11699 - 11702,4
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Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 46, p. 11531 - 11534[2] Angew. Chem., 2012, vol. 124, # 46, p. 11699 - 11702,4
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Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 46, p. 11531 - 11534[2] Angew. Chem., 2012, vol. 124, # 46, p. 11699 - 11702,4
  • 52
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Reference: [1] Synthesis, 1982, # 6, p. 464 - 465
  • 53
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Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 11, p. 3928 - 3939
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Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 11, p. 3928 - 3939
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Reference: [1] Arzneimittel-Forschung/Drug Research, 1996, vol. 46, # 12, p. 1154 - 1158
  • 56
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Reference: [1] Macromolecules, 2013, vol. 46, # 13, p. 5157 - 5166
  • 57
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Reference: [1] Macromolecules, 2013, vol. 46, # 13, p. 5157 - 5166
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 15, p. 4065 - 4068
  • 59
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Reference: [1] Patent: US5041674, 1991, A,
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  • [ 3260-88-6 ]
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Reference: [1] Patent: EP1044980, 2000, A1,
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YieldReaction ConditionsOperation in experiment
96.6% With phosgene In tetrachloromethane at 5 - 50℃; for 5.5 h; For 1000 ml three port in the reaction bottle, by adding 1,3-dimethyl-2-imidazolidinone (34.2 g, 0.3 mol), carbon tetrachloride (400 ml), stirring slowly dropwise solid phosgene carbon tetrachloride solution (containing solid phosgene 30 g, 0.1 mole, carbon tetrachloride 100 ml), the reaction mixture is kept below 5 °C, violent mixing 0.5 hours, the reaction at room temperature 1 hour, heating to 50 °C, maintain 4 hours. To be the reaction product is cooled to room temperature, filter, a small amount of carbon tetrachloride washing, get a pure white crystalline product chloropivaloyl 1,3-dimethyl-2-chlorotrifluoromethylbenzene imidazoline 49 g, yield of 96.6percent,
70.1% With oxalyl dichloride In benzene at 20℃; for 5 h; Inert atmosphere Under an inert atmosphere, 1,3-Dimethyl-2-imidazolidinone (7.0 mL, 64 mmol) was dissolved in anhydrous benzene (25 mL). To this oxalyl chloride (7.2 mL, 80 mmol) was added, and the solution was refluxed for 5 hours, and allowed to sit at room temperature overnight. The solution was filtered quickly to give 2-chloro-1,3-dimethylimidazolinium chloride (7.5815 g, 44.85 mmol) in 70.1percent yield.
53% at 140℃; for 5 h; 1,3-dimethyl-2-imidazolidinone 3.50g (30.7 mmol), and the mixture was heated for 5 hours and stirred at 140 of chloride phthalic acid 6.54g (32.4 mmol). After cooling, the crystal upon addition of 1,4-dioxane 25mL precipitated, filtered with a glass filter, washed twice with 1,4-dioxane 10 mL, washed once with ether 5 mL, and dried under vacuum. To give 2-chloro-1,3-dimethyl imidazolium chloride 2.72g (53percent yield).
Reference: [1] Patent: CN105367478, 2016, A, . Location in patent: Paragraph 0021; 0027; 0028
[2] European Journal of Inorganic Chemistry, 2005, # 19, p. 3815 - 3824
[3] Chemistry - A European Journal, 2016, vol. 22, # 45, p. 16187 - 16199
[4] Synthesis, 2009, # 13, p. 2267 - 2277
[5] Helvetica Chimica Acta, 1985, vol. 68, p. 1543 - 1556
[6] Journal of Organic Chemistry, 2018,
[7] Tetrahedron Letters, 2011, vol. 52, # 29, p. 3723 - 3725
[8] Angewandte Chemie - International Edition, 2014, vol. 53, # 44, p. 11907 - 11911[9] Angew. Chem., 2014, vol. 126, # 44, p. 12101 - 12105,5
[10] Journal of the American Chemical Society, 2006, vol. 128, # 43, p. 14185 - 14191
[11] Patent: JP5782331, 2015, B2, . Location in patent: Paragraph 0031
[12] Synlett, 2003, # 3, p. 369 - 371
[13] Chemical Communications, 2002, # 15, p. 1618 - 1619
[14] Synthesis, 2008, # 6, p. 917 - 920
[15] Journal of the American Chemical Society, [16] Journal of the American Chemical Society, 2009, vol. 131, p. 2882 - 2892
[17] European Journal of Inorganic Chemistry, 2011, # 8, p. 1302 - 1314
[18] Inorganica Chimica Acta, 2011, vol. 374, # 1, p. 546 - 557
[19] European Journal of Inorganic Chemistry, 2012, # 30, p. 4833 - 4845
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[23] Dalton Transactions, 2016, vol. 45, # 42, p. 16966 - 16983
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[27] Journal of Physical Organic Chemistry, 2018, vol. 31, # 8,
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Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 23, p. 8790 - 8797
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Reference: [1] Tetrahedron, 1986, vol. 42, # 24, p. 6645 - 6656
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Reference: [1] Organic Letters, 2000, vol. 2, # 23, p. 3539 - 3542
[2] Angewandte Chemie - International Edition, 2014, vol. 53, # 44, p. 11907 - 11911[3] Angew. Chem., 2014, vol. 126, # 44, p. 12101 - 12105,5
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YieldReaction ConditionsOperation in experiment
72% With methanesulfonic acid In water; 1,1'-carbonyldiimidazole EXAMPLE 6
Synthesis of N-(2-aminophenyl)-4-[N-(pyridin-3-ylmethoxycarbonyl)aminomethyl]benzamide (an example in which after activation with N,N'-carbonyldiimidazole, an acid was added to carry out reaction)
7.78 g (48 mmole) of N,N'-carbonyldiimidazole were added to a 1,3-dimethyl-2-imidazolidinone (50 g) suspension including 11.45 g (40 mmole) of 4-[N-(pyridin-3-ylmethoxycarbonyl)aminomethyl]benzoic acid.
After stirring at room temperature for 2 hours, 17.30 g (0.16 mole) of 1,2-phenylenediamine were added to the solution.
After cooling to 2° C., 9.60 g (0.1 mole) of methanesulfonic acid were added dropwise.
After stirring for 2 hours, water was added, and the deposited solid was collected by filtration.
Purification was then carried out through silica gel column chromatography to obtain 10.83 g (yield: 72percent) of N-(2-aminophenyl)-4-[N-(pyridin-3-ylmethoxycarbonyl)aminomethyl]benzamide.
Reference: [1] Patent: US6320078, 2001, B1,
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Reference: [1] Patent: US6166246, 2000, A,
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Reference: [1] Patent: US6166246, 2000, A,
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YieldReaction ConditionsOperation in experiment
12%
Stage #1: With bis(trichloromethyl) carbonate In tetrachloromethane at 20℃; for 5 h;
Stage #2: at -50℃;
A mixture of 1,3-dimethyl-2-imidazolidinone (20.7g, 0.18mol), triphosgene (15.14g, 0.051mol) in 50mL CCl4 was stirred at room temperature for 5h. The precipitate was filtered off, washed with hexane and dried in vacuum. To the product at the temperature −50° the NH3 (5ml) was added twice until complete evaporating of ammonia. Yield: 4.4g (12percent). Anal. Calc. for C5H13N3Cl·NH4Cl (204.12): , 29.42; H, 8.39; N, 27.45; Cl, 34.74. Found: , 28.98; H, 9.28; N, 27.74; Cl, 35.40percent.
Reference: [1] Polyhedron, 2016, vol. 106, p. 75 - 83
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Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

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Related Parent Nucleus of
[ 80-73-9 ]

Imidazolidines

Chemical Structure| 6281-42-1

[ 6281-42-1 ]

1-(2-Aminoethyl)imidazolidin-2-one

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Chemical Structure| 120-93-4

[ 120-93-4 ]

2-Imidazolidone

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Chemical Structure| 5391-39-9

[ 5391-39-9 ]

1-Acetylimidazolidin-2-one

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Chemical Structure| 87219-22-5

[ 87219-22-5 ]

2-(2-Oxoimidazolidin-1-yl)acetic acid

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Chemical Structure| 461-72-3

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Imidazolidine-2,4-dione

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