Structure of 80-73-9
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CAS No. : | 80-73-9 |
Formula : | C5H10N2O |
M.W : | 114.15 |
SMILES Code : | O=C1N(C)CCN1C |
MDL No. : | MFCD00003188 |
InChI Key : | CYSGHNMQYZDMIA-UHFFFAOYSA-N |
Pubchem ID : | 6661 |
GHS Pictogram: | ![]() ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302-H318-H361-H402 |
Precautionary Statements: | P201-P202-P264-P270-P273-P280-P301+P312+P330-P305+P351+P338+P310-P308+P313-P405-P501 |
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 ? Topological Polar Surface Area: Calculated from | 23.55 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 1.51 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | -0.49 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | -0.78 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 0.03 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | -0.19 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 0.01 |
Log S (ESOL):? ESOL: Topological method implemented from | -0.24 |
Solubility | 65.8 mg/ml ; 0.577 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (Ali)? Ali: Topological method implemented from | 0.46 |
Solubility | 331.0 mg/ml ; 2.9 mol/l |
Class? Solubility class: Log S scale | Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | 0.01 |
Solubility | 117.0 mg/ml ; 1.03 mol/l |
Class? Solubility class: Log S scale | Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg | Low |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg | No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) | No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) | No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) | No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) | No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) | No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) | No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from | -7.34 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from | 0.0 |
Ghose? Ghose filter: implemented from | None |
Veber? Veber (GSK) filter: implemented from | 0.0 |
Egan? Egan (Pharmacia) filter: implemented from | 0.0 |
Muegge? Muegge (Bayer) filter: implemented from | 1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat | 0.55 |
PAINS? Pan Assay Interference Structures: implemented from | 0.0 alert |
Brenk? Structural Alert: implemented from | 0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from | No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) | 1.34 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.6% | With phosgene; In tetrachloromethane; at 5 - 50℃; for 5.5h; | 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 96.6%, |
70.1% | With oxalyl dichloride; In benzene; at 20℃; for 5h;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 70.1% yield. |
53% | With Phthaloyl dichloride; at 140℃; for 5h; | 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 (53% yield). |
With oxalyl dichloride; In chloroform; for 20h;Reflux; Inert atmosphere; Schlenk technique; | To a solution of 1,3-dimethyl-2-imidazolidinone (1.0 mL, 9.3 mmol) dissolved in dry CHCl3 (20 mL) was added oxalyl chloride (3.9 mL,44.7 mmol) dropwise. The yellow solution was stirred at reflux for 20 h. The solvent was removed under vacuum. The remaining solid was washed twice with Et2O | |
With oxalyl dichloride; In toluene; at 80℃; for 12h;Inert atmosphere; | General procedure: N,N?-Disubstituted cyclic urea (6 mmol) was dissolved in toluene (50 mL) and oxalyl chloride (7.6 g, 5.2 mL, 60 mmol) was added. The resulting mixture was stirred at 80 C for 12 h. The white precipitate was then filtered off under an inert atmosphere, washed with anhydrous Et2O, and dried in vacuo to give the pure chloride as a white solid. | |
With oxalyl dichloride; In dichloromethane; at 0 - 20℃; for 6h;Inert atmosphere; | General procedure: A solution of urea (50mmol) in dry CH2Cl2 (10mL) was added dropwise at 0C under an Argon atmosphere to a solution of freshly distilled oxalyl chloride (55 mmoL) in dry CH2Cl2 (25ml). The reaction mixture was allowed to reach rt. and was stirred at rt 6h. The solvent was then evaporated under reduced pressure to afford a brown solid which was washed with dry Et2O (4×20mL) to give a white solid. | |
With oxalyl dichloride; In toluene; at 60℃; for 20h;Inert atmosphere; Cooling with ice; | General procedure: 1 ml urea derivatives dissolved in 400 ml toluene. 1.2 mol oxalyl chloride dissolved in toluene and then instilled to previous system in ice bath, protected by nitrogen and with strongly stirred. Then stirred in room temperature for 2h and heated in 60 for 20h. The mixture was cooled and filtered in reduced pressure, washed by ethyl acetate to get white solid. Needle-like crystal was harvested with 95%-97% yields after crystallization via ethyl acetate and acetonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35.9% | With triethylamine; trichlorophosphate; In water; acetonitrile; | Reference Example 8 2-Chloro-4-cyclopentylamino-6-nitroquinazoline To 300 mg (1.45 mmol) of 6-nitroquinazoline-2,4 (1H,3H)-dione were added 1 ml of 1,3-dimethyl-2-imidazolidinone and 1.23 g (8.05 mmol) of phosphorus oxychloride, and the resulting mixture was subjected to heating under reflux for 3 hours. After phosphorus oxychloride was removed in vacuo, the mixture was dissolved in 3 ml of acetonitrile, followed by addition of 4.05 ml (29.00 mmol) of triethylamine and 0.89 ml (8.70 mmol) of cyclopentylamine and stirring under ice cooling for 30 minutes. To the reaction solution was added water, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 152 mg (yield: 35.9%) of the title compound. NMR (delta, CDCl3): 1.58-1.90 (6H, m), 2.23-2.31 (2H, m), 4.66-4.74 (1H, m), 6.18 (1H, d, J=7 Hz), 7.85 (1H, d, J=9 Hz), 8.50 (1H, dd, J=9 Hz, 2 Hz), 8.68 (1H, d, J=2 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63.6% | With trichlorophosphate; In water; acetonitrile; | Reference Example 5 4-Butylamino-2-chloro-6-nitroquinazoline To 500 mg (2.41 mmol) of 6-nitroquinazoline-2,4 (1H,3H)-dione were added 2ml of 1,3-dimethyl-2-imidazolidinone and 8.23 g (53.64 mmol) of phosphorus oxychloride, and the resulting mixture was subjected to heating under reflux for 3 hours. After phosphorus oxychloride was removed in vacuo, the mixture was dissolved in 5 ml of acetonitrile, followed by addition of 5.9 ml (60 mmol) of butylamine and stirring under ice cooling for 30 minutes. To the reaction solution was added water, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 430 mg (yield: 63.6%) of the title compound. NMR (delta, CDCl3,): 1.02 (3H, t), 1.45-1.55 (2H, m), 1.73-1.81 (2H, m), 3.72-3.77 (2H, m), 6.30 (1H, br), 7.86 (1H, d, J=9 Hz), 8.51 (1H, dd, J=9 Hz, 2 Hz), 8.72 (1H, d, J=2 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; trichlorophosphate; In water; acetonitrile; | EXAMPLE 59 2-Allylamino-4-(3-methyl-2-butenylamino)-6-nitroquinazoline To 278 mg (1.45 mmol) of <strong>[32618-85-2]6-nitroquinazoline-2,4(1H,3H)-dione</strong> were added 0.71 ml of 1,3-dimethyl-2-imidazolidinone and 5.48 g (35.76 mmol) of phosphorus oxychloride, and the resulting mixture was subjected to heating under reflux for 3 hours. After phosphorus oxychloride was removed in vacuo, the mixture was dissolved in 3 ml of acetonitrile, followed by addition of 2.81 ml (20.0 mmol) of triethylamine and 267 mg (2.19 mmol) of 3-methyl-2-butenylamine hydrochloride and stirring under ice cooling for 2 hours. To the reaction solution was added water, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off to give 2-chloro-4-(3-methyl-2-butenylamino)-6-nitroquinazoline. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; trichlorophosphate; In water; acetonitrile; | EXAMPLE 62 2-Butylamino-4-(1-methyl-2-propenylamino)-6-nitroquinazoline To 278 mg (1.45 mmol) of <strong>[32618-85-2]6-nitroquinazoline-2,4(1H,3H)-dione</strong> were added 0.71 ml of 1,3-dimethyl-2-imidazolidinone and 5.48 g (35.76 mmol) of phosphorus oxychloride, and the resulting mixture was subjected to heating under reflux for 3 hours. After phosphorus oxychloride was removed in vacuo, the mixture was dissolved in 3 ml of acetonitrile, followed by addition of 2.81 ml (20.07 mmol) of triethylamine and 281 mg (2.61 mmol) of 1-methyl-2-propenylamine hydrochloride and stirring under ice cooling for 2 hours. To the reaction solution was added water, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off to give 2-chloro-4-(1-methyl-2-propenylamino)-6-nitroquinazoline. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13.0% | With triethylamine; trichlorophosphate; In water; acetonitrile; | Reference Example 4 2-Chloro-4-trans-cinnamylamino-6-nitroquinazoline To 400 mg (1.93 mmol) of 6-nitroquinazoline-2,4 (1H,3H)-dione were added 1 ml of 1,3-dimethyl-2-imidazolidinone and 2.96 g (19.3 mmol) of phosphorus oxychloride, and the resulting mixture was subjected to heating under reflux for 3 hours. After phosphorus oxychloride was removed in vacuo, the mixture was dissolved in 3 ml of acetonitrile, followed by addition of 5.94 ml (42.46 mmol) of triethylamine and 514 mg (3.86 mmol) of trans-cinnamylamine hydrochloride and stirring under ice cooling for 30 minutes. To the reaction solution was added water, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 85 mg (yield: 13.0%) of the title compound. NMR (delta, CDCl3); 4.43-4.46 (2H, m), 6.35-6.42 (1H, m), 6.67 (1H, d, J=16 Hz), 7.24-7.42 (5H, m), 7.77 (1H, d, J=9 Hz), 8.45 (1H, dd, J=9 Hz, 2 Hz), 9.11 (1H, br), 9.44 (1H, d, J=2 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.8% | With trichlorophosphate; In water; acetonitrile; | Reference Example 7 2-Chloro-4-heptylamino-6-nitroquinazoline To 300 mg (1.45 mmol) of 6-nitroquinazoline-2,4 (1H,3H)-dione were added 1 ml of 1,3-dimethyl-2-imidazolidinone and 2.22 g (14.48 mmol) of phosphorus oxychloride, and the resulting mixture was subjected to heating under reflux for 3 hours. After phosphorus oxychloride was removed in vacuo, the mixture was dissolved in 3 ml of acetonitrile, followed by addition of 5.38 ml (36.25 mmol) of heptylamine and stirring under ice cooling for 30 minutes. To the reaction solution was added water, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 247 mg (yield: 52.8%) of the title compound (yield: 52.8%). NMR (delta, CDCl3'): 0.89-0.92 (3H, m), 1.30-1.48 (8H, m), 1.74-1.81 (2H, m), 3.71-3.76 (2H, m), 6.20 (1H, br), 7.86 (1H, d, J=9 Hz), 8.51 (1H, dd, J=9 Hz, 2 Hz), 8.69 (1H, d, J=2 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94%; 100% | In toluene; | Example 11 Synthesis of lauroyl chloride To 93 g (0.55 mole) of <strong>[37091-73-9]2-chloro-1,3-dimethylimidazolinium chloride</strong>, 500 g of toluene and 100.2 g (0.5 mole) of lauric acid were added. The mixture was reacted at 110° C. for 4 hours. The reaction mass was analyzed by gas chromatography and liquid chromatography. The conversion ratio of lauric acid was 100percent, and the yield of lauroyl chloride was 100percent. Toluene was distilled from the reaction mass under reduced pressure and successively 56.5 g (0.495 mole) of 1,3-dimethylimidazolidine-2-one was recovered by distillation at 106°-108° C. under reduced pressure of 17 mmHg. Successively, 102.8 g (0.47 mole) of lauroyl chloride was obtained at 142°-144° C. under reduced pressure of 15 mmHg. The yield was 94percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine)palladium (0); | Example 6 Preparation of methyl 4-(1-fluorovinyl)-2-(trifluoromethyl)benzoate (C28) To a 100 mL round-bottomed flask was added <strong>[957207-58-8]methyl 4-bromo-2-(trifluoromethyl)benzoate</strong> (2.25 g, 8.00 mmol), (1-fluorovinyl)(methyl)diphenylsilane (3.58 g, 14.8 mmol), and 1,3-dimethylimidazolidin-2-one (40 mL). Tetrakis(triphenylphosphine)palladium(0) (0.459 g, 0.400 mmol), copper(I) iodide (0.0760 mg, 0.400 mmol), and cesium fluoride (3.62 g, 23.9 mmol) were added and the reaction was stirred at room temperature for 24 hours under a nitrogen atmosphere. Water was added to the mixture and the mixture was diluted with 3:1 hexanes/diethyl ether. The layer was separated, and the organic layer was dried over sodium sulfate, concentrated, and the residue was purified by flash column chromatography provided the title compound as a colorless oil (2.00 g, 96percent): 1H NMR (400 MHz, CDCl3) delta 7.96-7.87 (m, 1H), 7.83 (dq, J=8.1, 0.7 Hz, 1H), 7.77 (dd, J=8.2, 1.7 Hz, 1H), 5.23 (dd, J=48.6, 4.0 Hz, 1H), 5.07 (dd, J=17.4, 4.0 Hz, 1H), 3.95 (s, 3H); 19F NMR (376 MHz, CDCl3) delta -59.92, -108.73 (d, J=1.4 Hz); EIMS m/z 248 ([M]+). |
Tags: 80-73-9 synthesis path| 80-73-9 SDS| 80-73-9 COA| 80-73-9 purity| 80-73-9 application| 80-73-9 NMR| 80-73-9 COA| 80-73-9 structure
A139435 [6281-42-1]
1-(2-Aminoethyl)imidazolidin-2-one
Similarity: 0.96
A139435 [6281-42-1]
1-(2-Aminoethyl)imidazolidin-2-one
Similarity: 0.96
A234787 [87219-22-5]
2-(2-Oxoimidazolidin-1-yl)acetic acid
Similarity: 0.69
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H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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