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CAS No. : | 5918-93-4 | MDL No. : | MFCD00040252 |
Formula : | C3H4N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AICIYIDUYNFPRY-UHFFFAOYSA-N |
M.W : | 84.08 | Pubchem ID : | 22208 |
Synonyms : |
|
Num. heavy atoms : | 6 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 21.41 |
TPSA : | 48.65 Ų |
GI absorption : | High |
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) : | -7.42 cm/s |
Log Po/w (iLOGP) : | 0.63 |
Log Po/w (XLOGP3) : | -0.86 |
Log Po/w (WLOGP) : | -0.3 |
Log Po/w (MLOGP) : | -1.08 |
Log Po/w (SILICOS-IT) : | 1.42 |
Consensus Log Po/w : | -0.04 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.44 |
Solubility : | 30.8 mg/ml ; 0.366 mol/l |
Class : | Very soluble |
Log S (Ali) : | 0.32 |
Solubility : | 175.0 mg/ml ; 2.09 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -1.03 |
Solubility : | 7.81 mg/ml ; 0.0929 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
aluminium trichloride; In nitrobenzene; | EXAMPLE 14 4-Benzoyl-1,3-dihydro-2H-imidazol-2-one To 51 ml of nitrobenzene is added 1.68 g of 1,3-dihydro-2H-imidazol-2-one, 5.3 g of aluminum chloride and 3.1 g of benzoyl chloride. The mixture is stirred for 3 hours at 60° C. and poured into ice water. The solids are filtered, washed with ether and recrystallized twice from methyl alcohol-water to afford the title compound. M.P. 329°-30° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
aluminium trichloride; In nitrobenzene; | EXAMPLE 13 1,3-Dihydro-4-(2-thienoyl)-2H-imidazol-2-one In 50 ml of nitrobenzene is combined 13.3 g of aluminum chloride, 4.2 g of 1,3-dihydro-2H-imidazol-2-one and 8.1 g of thienoyl chloride. The mixture is stirred at 60° C. for 3 hours and poured over ice water. The solids are filtered, washed with ether and recrystallized twice from ethanol-water to afford the title compound. M.P. 339°-42° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With aluminum (III) chloride; In nitrobenzene; at 65℃; for 6h; | To a solution of dihydroimidazolone 1a (1.0 g, 11.9 mmol) in 24 mL 1M AlCl3 in nitrobenzene was added 2-nitrobenzoyl chloride (2.2 g, 11.9 mmol), and the reaction was heated in a 65° C. oil bath for 6 h. The reaction was poured over ice during which a solid formed. The reaction was filtered through a sintered glass funnel and the solid washed with water and diethyl ether and dried in vacuum dessicator to give 1.26 g (45percent yield) of 4-nitrobenzoyl-1,3-dihydroimidazol-2-one 1b. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 150℃; for 1.5h;microwave irradiation; | Example 145 1-(3-{2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-1, 3-dihydro-2H- imidazol-2-one dihydrochloride (E145); A mixture of 5-{4-T2-(3-IODOPHENYL) ETHYL]-1-PIPERAZINYL}-2-METHYLQUINOLINE (117 mg, 0.256 mmol), 1, 3-dihydro-2H-imidazol-2-one (84 mg, 1.023 mmol, Whitney, R. A. , Tet. Lett. 1981, 22,2063-2066), potassium carbonate (53 mg, 0.384 MMOL), copper (I) iodide (244 mg, 1.28 MMOL) and N, N'-dimethyl-1, 2-ethanediamine (163 CL, 135 mg, 1.536 MMOL) and dioxane (2.5 mL) was heated at 150°C for 90 min under microwave irradiation. The mixture was cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crude compound was purified by flash chromatography on silica gel, eluting with DICHLOROMETHANE-METHANOL (97: 3) affording the title compound in 20percent yield (23mg). The free base was converted into its DIHYDROCHLORIDE salt by dissolving the compound in DICHLOROMETHANE and adding a 1 M ethereal solution of HCI (2.1 eq) dropwise. A yellow solid precipitated and the suspension was stirred for 15 min. The solvent was removed under reduced pressure; the residue was triturated with ether. The title compound was then recovered by filtration (yield quantitative). MS: (ES/+) m/z: 414 [MH+] C25H27N5O requires 413. 1H-NMR (400MHZ, D6-DMSO) No. (ppm): 10.75 (1H, bs), 10.28 (s, 1H), 8.78 (bs, 1H), 7.84 (bs, 2H), 7.7 (bs, 1H), 7.69 (t, 1H), 7.56 (dd, 1H), 7. 38 (t, 1H), 7.36 (bs, 1H), 7.13 (d, 1H), 6.92 (dd, 1H), 6.58 (dd, 1H), 3.69 (bd, 2H), 3.5-3. 2 (8H), 3.12 (m, 2H), 2.81 (bs, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.4 g (12.6%) | With sodium hexamethyldisilazane; In di-isopropyl ether; water; N,N-dimethyl-formamide; 4-methyl-2-pentanone; | a) Sodium bis(trimethylsilyl)amide (5 ml) was added to a solution of 1,3-dihydro-2H-imidazol-2-one (0.84 g) in N,N-dimethylformamide (50 ml), stirred under a N2 flow and cooled in an ice-bath. The reaction mixture was stirred for 30 minutes. Intermediate 1 (2.69 g) was added portionwise and the resulting reaction mixture was stirred for 16 hours at RT, then for 2 hours at 50° C. The reaction mixture was stirred in methyl isobutyl ketone (200 ml)/(50 ml) water. The solvent was evaporated and methyl isobutyl ketone (100 ml) was added and azeotroped on the rotary evaporator. The mixture was purified by column chromatography over silica gel (eluent: CH2 Cl2 /(CH3 OH/NH3) 97/3). The desired fractions were collected and the solvent was evaporated. The white solid was stirred in diisopropyl ether, filtered off, washed with diisopropyl ether and dried, yielding 0.4 g (12.6percent) of 1-[2-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-oxoethyl]-1,3-dihydro-2H-imidazol-2-one (comp. 1; mp. 201.1° C.). |
0.4 g (12.6%) | With sodium hexamethyldisilazane; In water; N,N-dimethyl-formamide; 4-methyl-2-pentanone; | b) Sodium bis(trimethylsilyl)amide (5 ml) was added to a solution of 1,3-dihydro-2H-imidazol-2-one (0.84 g) in N,N-dimethylformamide (50 ml), stirred under a N2 flow and cooled in an ice-bath. The reaction mixture was stirred for 30 minutes. Intermediate 1 (2.69 g) was added portionwise and the resulting reaction mixture was stirred for 16 hours at RT, then for 2 hours at 50° C. The reaction mixture was stirred in methyl isobutyl ketone/water (200 ml/50 ml). The solvent was evaporated and methyl isobutyl ketone (100 ml) was added and azeotroped on the rotary evaporator. The mixture was purified by column chromatography over silica gel (eluent: CH2 Cl2 /(CH3 OH/NH3) 97/3). The desired fractions were collected and the solvent was evaporated. The white solid was stirred in DIPE, filtered off, washed with DIPE and dried, yielding 0.4 g (12.6percent) of 1-[2-[3-(cyclopentyloxy)-4methoxyphenyl]-2-oxoethyl]-1,3-dihydro-2H-imidazol-2-one (interm. 2; mp. 201.1° C.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
aluminium trichloride; In dichloromethane; | EXAMPLE 3 1,3-Dihydro-4-(1-oxobutyl)-2H-imidazol-2-one In 10 ml of dichloromethane is placed 1.0 g of 1,3-dihydro-2H-imidazol-2-one, 1.28 g of butyryl chloride and 4.8 g of aluminum chloride. The mixture is refluxed and stirred for 2 hours after which it is poured into water. The precipitate is collected, washed with water, and recrystallized from ethanol:water, to give the title compound, m.p. 268°-270° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride; In N,N-dimethyl-formamide; at 90℃; for 0.0833333h;Microwave irradiation; | Referring to Reaction Scheme 15, Stage 1, to a solution of 4-chloro-6-(3,4- dichloro-phenyl)-pyrimidine (leq) in DMF (20vol) was added sodium hydride (1.5eq) and imidazolone (1.5eq). The reaction mixture was heated at 90°C in a microwave for 5 minutes. To the cool mixture were added dichloromethane and a saturated solution of NaHCCb. The organic layer was separated and the aqueous layer was extracted further with dichloromethane. The organic layers were combined, dried with Na2S04, filtered and evaporated to dryness. Purification by flash column chromatography and trituration using an adequate solvent afforded the target compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; In tetrahydrofuran; at 20℃; for 0.166667h;Inert atmosphere; | General procedure: To a suspension of Cp2Zr(H)Cl (0.63 mmol) in anhydrous THF (2 mL) was added a substrate (0.31 mmol) in THF (1 mL) at room temperature and stirred under nitrogen for 1 h. Water (2 mL) was added to the mixture and kept stirring for 10 min. Then, it was extracted with EtOAc (20 mL), washed with brine, dried (Na2SO4) and evaporated under reduced pressure. The crude compound was purified by flash silica gel column chromatography to afford a pure product. Note: The reactions involving 9a?9d are treated with 2 N HCl for 10 min to affect the complete cleavage of the complex materials, and then neutralized with aqueous sat. NaHCO3 solution. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With piperazine; at 100℃; for 96h; | Synthesis of [Cd(D-ebimc)2]·4(H2O) (1D): The mixture of Cd(NO3)2·6H2O (1.0467g), D-Hebimc (1.0996g), NaOH (0.4204g) and distilled water (40mL) was sealed in a 100mL Teflon-lined autoclave and kept at 100°C for 4days. After cooling to room-temperature, the colourless crystals were obtained in pure phase (Yield: 40percent). Synthesis of [Cd(L-ebimc)2]·4(H2O) (1L): This phase was synthesized in an analogous procedure to 1D except that L-Hebimc was used in place of D-Hebimc. Synthesis of [Cd2(D-ebimc)4]·2(e-urea)·4(H2O) (2D): The mixture of Cd(NO3)2·6H2O (0.2047g), D-Hebimc (0.0869g), piperazine (0.0522g), e-urea (1.9657g) and distilled water (2.5mL) was sealed in a 20mL vial and kept at 100°C for 4days. After cooling to room-temperature, the colourless crystals were obtained in pure phase (yield: 35percent). Synthesis of [Cd2(L-ebimc)4]·2(e-urea)4(H2O) (2L): This phase was synthesized in an analogous procedure to 2D except that L-Hebimc was used in place of D-Hebimc. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With piperazine; at 100℃; for 96h; | Synthesis of [Cd(D-ebimc)2]·4(H2O) (1D): The mixture of Cd(NO3)2·6H2O (1.0467g), D-Hebimc (1.0996g), NaOH (0.4204g) and distilled water (40mL) was sealed in a 100mL Teflon-lined autoclave and kept at 100°C for 4days. After cooling to room-temperature, the colourless crystals were obtained in pure phase (Yield: 40percent). Synthesis of [Cd(L-ebimc)2]·4(H2O) (1L): This phase was synthesized in an analogous procedure to 1D except that L-Hebimc was used in place of D-Hebimc. Synthesis of [Cd2(D-ebimc)4]·2(e-urea)·4(H2O) (2D): The mixture of Cd(NO3)2·6H2O (0.2047g), D-Hebimc (0.0869g), piperazine (0.0522g), e-urea (1.9657g) and distilled water (2.5mL) was sealed in a 20mL vial and kept at 100°C for 4days. After cooling to room-temperature, the colourless crystals were obtained in pure phase (yield: 35percent). Synthesis of [Cd2(L-ebimc)4]·2(e-urea)4(H2O) (2L): This phase was synthesized in an analogous procedure to 2D except that L-Hebimc was used in place of D-Hebimc. Anal. Calcd for 1D, C20H26N4O10Cd (594.85): C, 40.38; H, 4.41; N, 9.41. Found: C, 39.87; H, 4.72; N, 9.73. IR (KBr, cm?1): 3404(w), 2367(w), 2406(w), 1665(m), 1634(m), 1543(s), 1479(s), 1388(s), 1309(m), 1123(m), 1054(w), 1003(w), 958(w), 905(w), 819(m), 788(m), 693(w), 624(w). Anal. Calcd for 2D, C46H52N12O18Cd2 (1285.8): C, 42.97; H, 4.07; N, 13.06. Found: C, 43.42; H, 4.26; N, 12.84. IR (KBr, cm?1): 3334(w), 2963(w), 2904(w), 1676(s), 1569(m), 1506(m), 1453(s), 1388(s), 1277(s), 1128(m), 1038(w), 995(w), 955(w), 905(m), 819(m), 767(w), 693(m), 517(m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of lH-imidazol-2(3H)-one (58.6 mg, 0.697 mmol) in 2.5 mL of DMSO was added NaH (60percent dispersion, 30.2 mg, 0.756 mmol). The reaction mixture was stirred at ambient temperature for 10 min before the addition of methyl 4-(bromomethyl)-3-(4- (5-isopropyl-l,3,4-thiadiazol-2-yl)phenoxy)benzoate (260 mg, 0.581 mmol) dissolved in 2.5 mL of DMSO. The reaction mixture was stirred at ambient temperature for 30 min and then quenched with water. The reaction mixture was then diluted with ethyl acetate and washed with water (3x's) and once with saturated aqueous sodium chloride. The combined organic layers were then dried over sodium sulfate and concentrated in vacuo. The crude material was purified via reverse-phase HPLC, eluting with 5percent acetonitrile in water (0.05percent NH4OH used as a modifier) initially, grading to 95percent acetonitrile in water. The desired fractions were concentrated to give the title compound. MS: mlz = 451.1 [M+l]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
240 mg | With caesium carbonate; In acetone; at 65℃; for 6h;Sealed tube; | Step 1. A mixture of lH-imidazol-2(3H)-one (100 mg, 1.19 mmol), cesium carbonate (853 mg, 2.62 mmol) and benzyl 2-bromoacetate (0.40 mL, 2.50 mmol) in acetone (10 mL) was sealed and heated in an oil bath at 65 °C for 6 h. The reaction mixture was filtered and concentrated in vacuo. The residual solid was purified by FCC (80 g silica gel, eluted with gradient 30percent~100percent EtOAc-hexanes) to afford dibenzyl 2,2'-(2-oxo-lH-imidazole- l,3(2H)-diyl)diacetate (240 mg) as a colorless oil. LC-MS retention time = 1.16 min; m/z = 381.3 [M+H]+. (Column: Waters Aquity BEH C18 2.1 X 50 mm 1.7^m-particles; Solvent A = 100percent Water/ 0.05percent TFA; Solvent B = 100percent Acetonitrile/0.05percent TFA; Flow Rate = 0.8 mL/min. Start percent B = 2; Final percent B = 98; Gradient Time = 1.5 minutes; Wavelength = 220 nm). NMR (400 MHZ, CDCh) delta ppm 7.46 - 7.32 (m, 10H), 6.33 (s, 2H), 5.22 (s, 4H), 4.48 (s, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
670 mg | With palladium diacetate; sodium acetate trihydrate; In dimethyl sulfoxide; at 80℃; for 16h;Inert atmosphere; | To a degassed (argon) solution of 1,3-dihydro-2H-imidazol-2-one (1.75 g, 18.75 mmol) and <strong>[64248-58-4]3,4-difluoroiodobenzene</strong> (3 g, 12.5 mmol) in dimethylsulfoxide (20 mL) was added, palladium(II) acetate (0.14 g, 0.62 mmol) and sodium acetate trihydrate (3.07 g, 37.5 mmol) at ambient temperature. The reaction mixture was further degassed with argon and stirred at 80 °C for 16 h. The reaction mixture was cooled to ambient temperature, filtered through Celite® diatomeaceaus earth filter aid and washed with ethyl acetate (2 × 50 mL). The filtrate was then washed with water (2 × 25 mL) and the crude product was purified by silica gel chromatography. Elution with 5percent methanol in dichloromethane provided the title compound as a white solid (670 mg). 1H NMR (400MHz) delta 6.97 (s, 1H), 7.34?7.44 (m, 2H), 7.55?7.61 (m, 1H), 10.12 (s, 1H), 10.54 (s, 1H). MS (M+1) = 195.2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With aluminum (III) chloride; In nitrobenzene; at 80℃; for 0.666667h;Microwave irradiation; | To a solution of lH-imidazol-2(3H)-one (56mg, 0.67mmol) in nitrobenzene (0.5ml) was added A1C13 (178mg, 1.34mmol) and 2,4-dichlorobenzoyl chloride (140.4mg, 0.67mmol). The mixture was heated to dissolve A1C13. The mixture was microwave irradiated at 80 °C for 40 min. To the mixture was added 50ml of ether and 60ml of 0.2 N NaOH. The aqueous layer was collected and neutralized with HCl. The cloudy solution was extracted with 50 ml of EtOAc. The organic layer was dried over Na2S04 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (EtOAc/hexane) to give 62 mg (40percent yield) of A. Compound A (62 mg, 0.24 mmol) was dissolved in 10 ml anhydrous DMF and treated with 28mu1 (0.192 mmol) of t-butyl bromoacetate and 180 mg of K2C03 (0.36 mmol). The mixture was stirred at 50 °C overnight. After the reaction solvent was evaporated, the residues was dissolved with EtOAc and washed successively with water and brine. The organic layer was dried over Na2S04 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (EtOAc/hexane) to obtain B in 60percent yield (53 mg, 0.144 mmol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With tris(dibenzylideneacetone)dipalladium (0) chloroform adduct; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 60℃; for 5h;Inert atmosphere; | To a solution of 2-bromo-6-(4-isopropyl-4i/-l,2,4-triazol-3-yl)pyridine (200 mg, 0.75 mmol) in DMF (5 mL) was added 2,3-dihydro- li/-imidazol-2-one (94.4 mg, 1.12 mmol), Pd2(dba)3.CHCb (77.5 mg, 0.08 mmol), Xantphos (86.6 mg, 0.15 mmol) and CS2CO3 (731.8 mg, 2.25 mmol). The resulting mixture was stirred at 60°C for 5 h under N2 atmosphere. The resulting mixture was diluted with H2O and extracted with ethyl acetate. (0291) The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum. The residue was purified by flash column chromatography with dichloromethane/methanol (10/1, v/v) to afford the title compound (100 mg, 49percent) as a yellow solid. LCMS (ESI, m/z): [M+H]+ = 271.2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | General procedure: To a solution of 1,3-dihydro-2H-imidazol-2-one (10,12 mg, 0.143 mmol) in DMF (1 mL) was added at 0 C NaH (60% in mineral oil,17.1 mg, 0.428 mmol). The suspension was warmed to rt over 30 min and thencooled to 0 C. To this was added ArSO2Cl (0.314 mmol). The solutionwas allowed to warm to rt over 12 h, at which point the reaction was quenchedby addition of brine (1 mL). The aqueous layer was separated and extracted withEtOAc (3×2 mL). The combined organic layers were washed with brine (3 mL),dried over Na2SO4, filtered, and concentrated in vacuo.The crude mixture was purified by column chromatography (gradient 0% to 100%EtOAc in hexanes) to afford bis(arylsulfonyl)dihydroimidazolinones (9a-9ac). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | General procedure: To a solution of 1,3-dihydro-2H-imidazol-2-one (10,12 mg, 0.143 mmol) in DMF (1 mL) was added at 0 C NaH (60% in mineral oil,17.1 mg, 0.428 mmol). The suspension was warmed to rt over 30 min and thencooled to 0 C. To this was added ArSO2Cl (0.314 mmol). The solutionwas allowed to warm to rt over 12 h, at which point the reaction was quenchedby addition of brine (1 mL). The aqueous layer was separated and extracted withEtOAc (3×2 mL). The combined organic layers were washed with brine (3 mL),dried over Na2SO4, filtered, and concentrated in vacuo.The crude mixture was purified by column chromatography (gradient 0% to 100%EtOAc in hexanes) to afford bis(arylsulfonyl)dihydroimidazolinones (9a-9ac). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | General procedure: To a solution of 1,3-dihydro-2H-imidazol-2-one (10,12 mg, 0.143 mmol) in DMF (1 mL) was added at 0 C NaH (60% in mineral oil,17.1 mg, 0.428 mmol). The suspension was warmed to rt over 30 min and thencooled to 0 C. To this was added ArSO2Cl (0.314 mmol). The solutionwas allowed to warm to rt over 12 h, at which point the reaction was quenchedby addition of brine (1 mL). The aqueous layer was separated and extracted withEtOAc (3×2 mL). The combined organic layers were washed with brine (3 mL),dried over Na2SO4, filtered, and concentrated in vacuo.The crude mixture was purified by column chromatography (gradient 0% to 100%EtOAc in hexanes) to afford bis(arylsulfonyl)dihydroimidazolinones (9a-9ac). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | General procedure: To a solution of 1,3-dihydro-2H-imidazol-2-one (10,12 mg, 0.143 mmol) in DMF (1 mL) was added at 0 C NaH (60% in mineral oil,17.1 mg, 0.428 mmol). The suspension was warmed to rt over 30 min and thencooled to 0 C. To this was added ArSO2Cl (0.314 mmol). The solutionwas allowed to warm to rt over 12 h, at which point the reaction was quenchedby addition of brine (1 mL). The aqueous layer was separated and extracted withEtOAc (3×2 mL). The combined organic layers were washed with brine (3 mL),dried over Na2SO4, filtered, and concentrated in vacuo.The crude mixture was purified by column chromatography (gradient 0% to 100%EtOAc in hexanes) to afford bis(arylsulfonyl)dihydroimidazolinones (9a-9ac). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | Stage #1: 1,3-dihydroimidazolone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 3-[(trifluoromethyl)oxy]benzenesulfonyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 12h; Inert atmosphere; | Bis(arylsulfonyl)dihydroimidazolinones (9a-9ac) General procedure: To a solution of 1,3-dihydro-2H-imidazol-2-one (10,12 mg, 0.143 mmol) in DMF (1 mL) was added at 0 °C NaH (60% in mineral oil,17.1 mg, 0.428 mmol). The suspension was warmed to rt over 30 min and thencooled to 0 °C. To this was added ArSO2Cl (0.314 mmol). The solutionwas allowed to warm to rt over 12 h, at which point the reaction was quenchedby addition of brine (1 mL). The aqueous layer was separated and extracted withEtOAc (3×2 mL). The combined organic layers were washed with brine (3 mL),dried over Na2SO4, filtered, and concentrated in vacuo.The crude mixture was purified by column chromatography (gradient 0% to 100%EtOAc in hexanes) to afford bis(arylsulfonyl)dihydroimidazolinones (9a-9ac). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | General procedure: To a solution of 1,3-dihydro-2H-imidazol-2-one (10,12 mg, 0.143 mmol) in DMF (1 mL) was added at 0 C NaH (60% in mineral oil,17.1 mg, 0.428 mmol). The suspension was warmed to rt over 30 min and thencooled to 0 C. To this was added ArSO2Cl (0.314 mmol). The solutionwas allowed to warm to rt over 12 h, at which point the reaction was quenchedby addition of brine (1 mL). The aqueous layer was separated and extracted withEtOAc (3×2 mL). The combined organic layers were washed with brine (3 mL),dried over Na2SO4, filtered, and concentrated in vacuo.The crude mixture was purified by column chromatography (gradient 0% to 100%EtOAc in hexanes) to afford bis(arylsulfonyl)dihydroimidazolinones (9a-9ac). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | General procedure: To a solution of 1,3-dihydro-2H-imidazol-2-one (10,12 mg, 0.143 mmol) in DMF (1 mL) was added at 0 C NaH (60% in mineral oil,17.1 mg, 0.428 mmol). The suspension was warmed to rt over 30 min and thencooled to 0 C. To this was added ArSO2Cl (0.314 mmol). The solutionwas allowed to warm to rt over 12 h, at which point the reaction was quenchedby addition of brine (1 mL). The aqueous layer was separated and extracted withEtOAc (3×2 mL). The combined organic layers were washed with brine (3 mL),dried over Na2SO4, filtered, and concentrated in vacuo.The crude mixture was purified by column chromatography (gradient 0% to 100%EtOAc in hexanes) to afford bis(arylsulfonyl)dihydroimidazolinones (9a-9ac). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | Stage #1: 1,3-dihydroimidazolone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 3,4-difluorobenzenesulfonyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 12h; Inert atmosphere; | Bis(arylsulfonyl)dihydroimidazolinones (9a-9ac) General procedure: To a solution of 1,3-dihydro-2H-imidazol-2-one (10,12 mg, 0.143 mmol) in DMF (1 mL) was added at 0 °C NaH (60% in mineral oil,17.1 mg, 0.428 mmol). The suspension was warmed to rt over 30 min and thencooled to 0 °C. To this was added ArSO2Cl (0.314 mmol). The solutionwas allowed to warm to rt over 12 h, at which point the reaction was quenchedby addition of brine (1 mL). The aqueous layer was separated and extracted withEtOAc (3×2 mL). The combined organic layers were washed with brine (3 mL),dried over Na2SO4, filtered, and concentrated in vacuo.The crude mixture was purified by column chromatography (gradient 0% to 100%EtOAc in hexanes) to afford bis(arylsulfonyl)dihydroimidazolinones (9a-9ac). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | General procedure: To a solution of 1,3-dihydro-2H-imidazol-2-one (10,12 mg, 0.143 mmol) in DMF (1 mL) was added at 0 C NaH (60% in mineral oil,17.1 mg, 0.428 mmol). The suspension was warmed to rt over 30 min and thencooled to 0 C. To this was added ArSO2Cl (0.314 mmol). The solutionwas allowed to warm to rt over 12 h, at which point the reaction was quenchedby addition of brine (1 mL). The aqueous layer was separated and extracted withEtOAc (3×2 mL). The combined organic layers were washed with brine (3 mL),dried over Na2SO4, filtered, and concentrated in vacuo.The crude mixture was purified by column chromatography (gradient 0% to 100%EtOAc in hexanes) to afford bis(arylsulfonyl)dihydroimidazolinones (9a-9ac). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Stage #1: 1,3-dihydroimidazolone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 2,4,5-trifluorobenzene-1-sulfonyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 12h; Inert atmosphere; | Bis(arylsulfonyl)dihydroimidazolinones (9a-9ac) General procedure: To a solution of 1,3-dihydro-2H-imidazol-2-one (10,12 mg, 0.143 mmol) in DMF (1 mL) was added at 0 °C NaH (60% in mineral oil,17.1 mg, 0.428 mmol). The suspension was warmed to rt over 30 min and thencooled to 0 °C. To this was added ArSO2Cl (0.314 mmol). The solutionwas allowed to warm to rt over 12 h, at which point the reaction was quenchedby addition of brine (1 mL). The aqueous layer was separated and extracted withEtOAc (3×2 mL). The combined organic layers were washed with brine (3 mL),dried over Na2SO4, filtered, and concentrated in vacuo.The crude mixture was purified by column chromatography (gradient 0% to 100%EtOAc in hexanes) to afford bis(arylsulfonyl)dihydroimidazolinones (9a-9ac). |
Tags: 5918-93-4 synthesis path| 5918-93-4 SDS| 5918-93-4 COA| 5918-93-4 purity| 5918-93-4 application| 5918-93-4 NMR| 5918-93-4 COA| 5918-93-4 structure
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
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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