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[ CAS No. 694-32-6 ] {[proInfo.proName]}

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Chemical Structure| 694-32-6
Chemical Structure| 694-32-6
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Product Details of [ 694-32-6 ]

CAS No. :694-32-6 MDL No. :MFCD00800601
Formula : C4H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :JTPZTKBRUCILQD-UHFFFAOYSA-N
M.W : 100.12 Pubchem ID :567600
Synonyms :
2-imidazolidinone, 1-methyl-

Calculated chemistry of [ 694-32-6 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 33.34
TPSA : 32.34 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) : -7.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.12
Log Po/w (XLOGP3) : -0.67
Log Po/w (WLOGP) : -1.12
Log Po/w (MLOGP) : -0.38
Log Po/w (SILICOS-IT) : 0.04
Consensus Log Po/w : -0.2

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.04
Solubility : 91.6 mg/ml ; 0.915 mol/l
Class : Very soluble
Log S (Ali) : 0.46
Solubility : 292.0 mg/ml ; 2.92 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.29
Solubility : 50.8 mg/ml ; 0.507 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.25

Safety of [ 694-32-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 694-32-6 ]

* 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 [ 694-32-6 ]
  • Downstream synthetic route of [ 694-32-6 ]

[ 694-32-6 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 74378-14-6 ]
  • [ 694-32-6 ]
YieldReaction ConditionsOperation in experiment
68% With sodium hydride In tetrahydrofuran at 20℃; for 18 h; Inert atmosphere To a solution of l-(2-chloroethyl)-3-methylurea (3 g, 22 mmol) was dissolved in THF (80 mL) and to the resulting solution was added NaH (2.2 g, 55 mmol). The reaction mixture was stirred at room temperature under N2 for 18 hours, quenched with MeOH, filtrated, the filtrate was dried with Na2S04, concentrated in vacuo to provide l-methylimidazolidin-2-one (1.5 g, yield: 68percent). MS (M+H)+: 101.
68% With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 18 h; Inert atmosphere Step 2-Synthesis of 1-methylimidazolidin-2-one
To a solution of 1-(2-chloroethyl)-3-methylurea (3 g, 22 mmol) was dissolved in THF (80 mL) and to the resulting solution was added NaH (2.2 g, 55 mmol).
The reaction mixture was stirred at room temperature under N2 for 18 hours, quenched with MeOH, filtrated, the filtrate was dried with Na2SO4, concentrated in vacuo to provide 1-methylimidazolidin-2-one (1.5 g, yield: 68percent). MS (M+H)+: 101.
Reference: [1] Patent: WO2013/33971, 2013, A1, . Location in patent: Page/Page column 185
[2] Patent: US2014/213571, 2014, A1, . Location in patent: Paragraph 0723
[3] Patent: WO2010/45303, 2010, A2, . Location in patent: Page/Page column 95-96
[4] Patent: US2013/281451, 2013, A1, . Location in patent: Paragraph 0234
  • 2
  • [ 120-93-4 ]
  • [ 74-88-4 ]
  • [ 694-32-6 ]
YieldReaction ConditionsOperation in experiment
36%
Stage #1: With sodium hydride In 1,4-dioxane; mineral oil at 20℃; for 0.5 h; Inert atmosphere; Cooling with ice
Stage #2: at 20℃; for 5.5 h; Inert atmosphere; Cooling with ice
15.3 g (177 mmol) of 2-imidazolidone was dissolved in 200 mL of 1,4-dioxane in a 500 mL eggplant flask equipped with an argon gas balloon and cooled on ice, 9.30 g (212 mmol (55percent oil suspension) of sodium hydride ) Was added and the mixture was stirred at room temperature for 30 minutes.Under ice cooling, 20.4 mL (328 mmol) of iodomethane was added and the mixture was stirred for 30 minutes and then stirred at room temperature for 5 hours. The precipitated salt was filtered off, the filtrate was concentrated and the residue was purified by silica gel column chromatography (developing solution: chloroform / methanol = 10/1) to obtain 6.4 g of 1-methyl-2-imidazolidone colorless solid (Yield: 36percent).
Reference: [1] Journal of Organometallic Chemistry, 2001, vol. 617-618, p. 182 - 208
[2] Patent: JP2016/145198, 2016, A, . Location in patent: Paragraph 0085; 0086
[3] Angewandte Chemie - International Edition, 2017, vol. 56, # 33, p. 9842 - 9846[4] Angew. Chem., 2017, vol. 129, # 33, p. 9974 - 9978,5
[5] Organic Mass Spectrometry, 1989, vol. 24, p. 718 - 722
  • 3
  • [ 57-13-6 ]
  • [ 109-81-9 ]
  • [ 694-32-6 ]
YieldReaction ConditionsOperation in experiment
71.1% at 130℃; for 8 h; 13.0 mL (149 mmol) of N-methylethylenediamine, 9.01 g (150 mmol) of urea and 10 mL of ethylene glycol were added to a 100 mL recovery flask, and the mixture was stirred at 130 ° C. for 8 hours. Ethylene glycol was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (developing solution: chloroform / methanol = 10/1) to obtain 10.6 g of colorless solid 1-methyl-2-imidazolidone : 71.1percent)
Reference: [1] Patent: JP2016/145198, 2016, A, . Location in patent: Paragraph 0075; 0076
[2] Tetrahedron Letters, 2004, vol. 45, # 39, p. 7205 - 7208
  • 4
  • [ 124-38-9 ]
  • [ 109-81-9 ]
  • [ 694-32-6 ]
Reference: [1] Green Chemistry, 2013, vol. 15, # 6, p. 1567 - 1577
[2] Journal of Organic Chemistry, 1992, vol. 57, # 28, p. 7339 - 7342
  • 5
  • [ 616-38-6 ]
  • [ 109-81-9 ]
  • [ 694-32-6 ]
Reference: [1] Patent: WO2013/12995, 2013, A1, . Location in patent: Page/Page column 21-22
[2] Patent: EP2548869, 2013, A1, . Location in patent: Paragraph 0047; 0048
  • 6
  • [ 107-15-3 ]
  • [ 616-38-6 ]
  • [ 120-93-4 ]
  • [ 694-32-6 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: at 50℃; for 3 h; Green chemistry
Stage #2: at 160℃; for 15 h; Green chemistry
A mixture of 1,2-ethylenediamine (3.0 g, 0.05 mol), dimethyl carbonate (5.4 g, 0.06 mol),sulfamic acid (1.0 g, 0.01 mol) and 4.5 ml of methanol in an autoclave (100 ml, fitted witha thermocouple to measure the temperature and a magnetic stirrer, at 20–60 bar)19 washeated to and kept at 50oC for 3 h (CAUTION). The internal temperature was then raisedto 160oC and maintained at that temperature for 15 h. After that time, heating was stoppedand the system was allowed to cool to room temperature. The low boiling point substanceswere distilled off under vacuum (7.5 mm Hg). Then, acetone (15 ml) was added to the solidresidue and the suspension was stirred for 10 minutes at room temperature. The suspensionwas filtered to remove insoluble material and the filtrate was distilled off under vacuum(7.5 mm Hg) to give 3.0 g (70percent) 2-imidazolidinone as a white solid, mp. 130–132C, lit.20mp. 130–131oC. 1H NMR (400 MHz, CDCl3): δ 3.53 (s, 4H, CH2), 5.37 (s, 2H, NH); 13CNMR (100MHz, CDCl3): δ 40.94, 165.35.
Reference: [1] Organic Preparations and Procedures International, 2014, vol. 46, # 5, p. 453 - 456
  • 7
  • [ 13431-10-2 ]
  • [ 694-32-6 ]
Reference: [1] Journal of Molecular Structure, 1981, vol. 77, p. 239 - 252
[2] Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 1983, vol. 39, # 10, p. 929 - 932
  • 8
  • [ 120-93-4 ]
  • [ 80-48-8 ]
  • [ 694-32-6 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 6409,6412
  • 9
  • [ 23589-75-5 ]
  • [ 109-81-9 ]
  • [ 694-32-6 ]
Reference: [1] Synthesis, 1983, # 12, p. 1032 - 1033
  • 10
  • [ 74378-14-6 ]
  • [ 1333-74-0 ]
  • [ 694-32-6 ]
Reference: [1] Patent: US2018/346438, 2018, A1,
  • 11
  • [ 865-47-4 ]
  • [ 694-32-6 ]
  • [ 637-92-3 ]
  • [ 61076-69-5 ]
Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 11, p. 3928 - 3939
  • 12
  • [ 120-93-4 ]
  • [ 77-78-1 ]
  • [ 694-32-6 ]
Reference: [1] Journal of Organic Chemistry, 1959, vol. 24, p. 645,647
  • 13
  • [ 67-56-1 ]
  • [ 694-32-6 ]
  • [ 115-10-6 ]
  • [ 540-67-0 ]
  • [ 61076-69-5 ]
Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 11, p. 3928 - 3939
  • 14
  • [ 75-65-0 ]
  • [ 694-32-6 ]
  • [ 637-92-3 ]
  • [ 61076-69-5 ]
Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 11, p. 3928 - 3939
  • 15
  • [ 61076-89-9 ]
  • [ 107-95-9 ]
  • [ 694-32-6 ]
  • [ 99645-98-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1985, p. 1255 - 1264
[2] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1985, p. 1255 - 1264
  • 16
  • [ 75697-81-3 ]
  • [ 694-32-6 ]
  • [ 13431-10-2 ]
  • [ 2461-80-5 ]
  • [ 2461-75-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1773 - 1778
  • 17
  • [ 87768-63-6 ]
  • [ 694-32-6 ]
  • [ 14609-74-6 ]
  • [ 109-81-9 ]
Reference: [1] Tetrahedron, 1985, vol. 41, # 16, p. 3269 - 3284
  • 18
  • [ 164115-06-4 ]
  • [ 694-32-6 ]
  • [ 75-01-4 ]
  • [ 75-07-0 ]
  • [ 107-06-2 ]
Reference: [1] Synthesis, 1996, # 10, p. 1246 - 1258
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