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CAS No. : | 3291-03-0 | MDL No. : | MFCD00014758 |
Formula : | C10H14N2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 226.23 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 56.81 |
TPSA : | 82.81 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) : | -7.35 cm/s |
Log Po/w (iLOGP) : | 1.79 |
Log Po/w (XLOGP3) : | 0.46 |
Log Po/w (WLOGP) : | 0.32 |
Log Po/w (MLOGP) : | 0.39 |
Log Po/w (SILICOS-IT) : | 0.29 |
Consensus Log Po/w : | 0.65 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.48 |
Solubility : | 7.49 mg/ml ; 0.0331 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.77 |
Solubility : | 3.86 mg/ml ; 0.0171 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.43 |
Solubility : | 0.841 mg/ml ; 0.00372 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.84 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
90% | With hydrazine hydrate In ethanol Reflux; | 1.b; 4.b; 6.b b) Synthesis of compound 5: Ethyl 3,4,5-trimethoxybenzoate 3 (2.40 g, 0.01 mol) was dissolved in EtOH, then hydrazide hydrate 4 (1.93 ml, 0.04 mol) was added slowly with gentle stirring. After the addition was complete, the reaction solution was refluxed overnight and the reaction was monitored by TLC until starting material disappeared. Then the reaction was cooled down to room temperature, the precipitate was filtered off and crystallized from alcohol to give product 5 (2.0 g, 90%). NMR (400 MHz; CDCh) d 3.65 (3H, s), 3.66 (6H, s), 4.44 (1H, s), 7.16 (2H, s), 9.69 (1H, s). 13 C NMR (200 MHz; CDCh) d 56.4, 60.5, 104.4, 128.9, 140.1, 153.0, 165.8. |
89% | With hydrazine hydrate In ethanol for 6h; Heating; | |
85% | With hydrazine hydrate In ethanol Reflux; | General method for the preparation of benzohydrazides ( 21-25 ) and 2-henylbenzohydrazides (26-30) General procedure: Ethylbenzoates (11-15, 1.5g, 9.98 mmol)and ethyl-2-phenylacetates (16-20, 1.5g, 9.13 mmol)were dissolved in ethanol and then hydrazine-hydrate(99%) was added and reux for 8-12h. Ethanol wasconcentrated and the resultant residue was pouredin ice cold water and stirred for 15 -20 min, the solidsthat were thrown out was fltered at the pump anddried to obtain the corresponding benzohydrazides(21-25) and 2-phenylacetohydrazides (26-30) in 80-82% yield. |
72.9% | With hydrazine hydrate In ethanol Reflux; | 5 4.1.2 General procedure for the synthesis of substituted benzohydrazides 3a-e [58,59] General procedure: A solution of the isolated esters 2a-e (10mmol) in ethanol (20mL), hydrazine hydrate (97%, 3mL) was added and heated under reflux for 5-8h. After cooling, the formed precipitate was filtered off, washed with water, dried, and crystallized from ethanol. |
72.9% | With hydrazine hydrate In ethanol Reflux; | 4.1.2. General procedure for the synthesis of substitutedbenzohydrazides 3a-e General procedure: Hydrazine hydrate (97%, 30 mmol, 1.5 mL) was added to a solutionof the isolated esters 2a-e (10 mmol) in ethanol (20 mL), and themixture was heated at reflux for 5-8 h. After cooling, the resultingprecipitate was filtered off, washed with water, dried, and crystallizedfrom ethanol. |
64% | With hydrazine hydrate In ethanol Heating; | |
With ethanol; hydrazine hydrate | ||
With diethyl ether; hydrazine hydrate | ||
With hydrazine In ethanol for 3h; Heating; | ||
With hydrazine hydrate for 6h; Heating; | ||
With hydrazine hydrate for 8h; Heating; | ||
With hydrazine hydrate for 8h; Reflux; | ||
With hydrazine hydrate In ethanol for 8h; Reflux; | ||
With hydrazine hydrate In ethanol Reflux; | ||
With hydrazine hydrate | ||
With hydrazine hydrate for 7h; Reflux; | ||
With hydrazine hydrate In ethanol Microwave irradiation; | ||
With hydrazine hydrate In ethanol for 6h; Reflux; | Preparation of 3,4,5-trimethoxybenzohydrazide (I) To a 100 mL round-bottom flask, 3,4,5-trimethoxybenzoic acid (10.6g, 50 mmol), 1 mL of concentrated sulfuric acid and 30 mL of ethanol were added gradually. The resulting mixture was stirred at reflux for 12 h and was then concentrated on a rotary evaporator. The crude product obtained was poured into 50 ml of water and extracted with ethyl acetate (30 mL×3). The combined ethyl acetate extracts were washed with water (30 mL×2), dried with anhydrous magnesium sulfate, filtered off by suction and the solvent was evaporated to give crude ethyl 3,4,5-trimethoxybenzoate, which and hydrazine hydrate (7.5 g, 150 mmol, 60%) in 50 mL of ethanol was heated under reflux for 6 h. Excess ethanol was distilled out and the contents were allowed to cool. The solid product obtained was filtered, washed thoroughly with water, and dried to give II in total yield of 83%, which was used for the next reactions without further purification. | |
With hydrazine hydrate In ethanol Reflux; | ||
With hydrazine hydrate In ethanol | ||
With hydrazine hydrate In ethanol for 6.5h; Reflux; | 4.1.4 General procedure for the preparation of substituted benzohydrazide (13a-g) General procedure: A mixture of substituted ethyl benzoate (12a-g) (0.1M) and hydrazine hydrate (0.3M) was heated under reflux for 30min. Ethanol (20mL) was added to the refluxing mixture as a solvent in order to homogenize the solution, the resulting mixture was further allowed for 6h. Excess of ethanol was distilled out and the content was allowed to cool. The crystals formed were filtered and washed thoroughly with water and dried. | |
With hydrazine hydrate In ethanol at 85℃; | ||
With hydrazine hydrate In ethanol Heating; Inert atmosphere; | ||
With hydrazine hydrate In ethanol for 8h; Reflux; | General procedure for the synthesis of benzohydrazides7a-k [12,13] General procedure: A mixture of benzoic acid (6.42 mmol), catalytic quantity of conc. H2SO4 in ethanol was heated to reflux for 10 h. The reaction mixture was diluted with ethyl acetate followed by water. The organic layer was washed with saturated NaHCO3 followed by water and brine solution. The organic layer was dried over sodium sulphate, filtered and evaporated to obtain respective ethyl benzoates. To a stirred solution of ethyl benzoates (5 mmol) in ethanol was added hydrazine-hydrate (12.5 mmol) and refluxed for 8 h. The reaction mixture was diluted with ethyl acetate followed by water. The organic layer was dried over sodium sulphate, filtered and evaporated to obtain respective benzohydrazides 7a-k. | |
With H4N2*5H2O In ethanol at 70℃; for 6h; | ||
With hydrazine hydrate In ethanol for 8h; Reflux; | Experimental procedure for synthesis of benzohydrazides7a-j [34-35] General procedure: Benzoic acids a-j(8.12 mmol) was dissolved in ethanol (15 mL) and added catalytic qty of conc.H2SO4and heated to reflux for 10 h. Ethanol was evaporated and the obtained residue was diluted with ethylacetate (25 mL). The organic layer was washed with aqueous saturated NaHCO3(3 X 15 mL) followed by water (2 X 15 mL) and brine solution (20 mL). The organic layer was separated, dried over sodium sulphate, filtered and evaporated to obtain respective ethyl benzoates.To the above prepared respective ethyl benzoates (6.65 mmol) in ethanol was added hydrazine-hydrate (40.0 mmol) and refluxed for 8 h. Ethanol was evaporated from the reaction mixture and the precipitated solids were slurred with petether (5 times) and filtered at the pump and dried to obtain benzohydrazides7a-7j. | |
With hydrazine hydrate In ethanol for 6h; Reflux; | 5.1.1. General procedure for the target compounds 5~6 General procedure: To a 100 mL round-bottom flask, 3,4,5-trimethoxybenzoic acid(10.6 g, 50 mmol), 1 mL of concentrated sulfuric acid and 30 mL ofethanol were added gradually. The resulting mixture was stirred atreflux for 12 h and was then concentrated on a rotary evaporator.The crude product obtained was poured into 50 mL of water andextracted with ethyl acetate. The combined ethyl acetate extractswere washed with water, dried with anhydrous magnesium sulfatefiltered off by suction and the solvent was evaporated to give crudeethyl 3,4,5-trimethoxybenzoate, which and hydrazine hydrate(7.5 g, 150 mmol, 60%) in 50 mL of ethanol was heated under refluxfor 6 h. Excess ethanol was distilled out and the contents wereallowed to cool. The solid product obtained was filtered, washedthoroughly with water, and dried to give 3,4,5-trimethoxybenzohydrazide in total yield of 83%, which was usedfor the next reactions without further purification. A solution of3,4,5-trimethoxybenzohydrazide (3.39 g, 15 mmol) and appropriateisothiocyanatobenzenes (15 mmol) in ethanol (40 mL) washeated at reflux for 1 h, then cooled at room temperature. Thesuspensionwas filtered, and the solidwaswashed with ethanol anddried to give the intermediate hydrazinecarbothioamide as whitesolid. Then 1 N NaOH (30 mL) was added to this solid and themixture was heated at reflux for 1 h. The resulting solution wascooled at room temperature and acidified to pH 5e6 with 1 M HCl.The precipitatewas filtered,washed withwater, and dried to obtainthe title compounds as white solid. | |
With hydrazine hydrate In ethanol for 10h; Reflux; | ||
With hydrazine hydrate | ||
With hydrazine In ethanol Inert atmosphere; | ||
With hydrazine hydrate In ethanol Reflux; | ||
With hydrazine hydrate In ethanol for 12h; Reflux; | ||
With hydrazine In methanol for 7h; Reflux; | ||
With hydrazine hydrate Reflux; | ||
With hydrazine hydrate | ||
16.10 g | With hydrazine hydrate In ethanol Reflux; | |
With H4N2*5H2O In ethanol Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.2% | With hydrazine at 92℃; for 4h; | 9.1 Preparation of 3,4,5-trimethoxybenzohydrazide Preparation of 3,4,5-trimethoxybenzohydrazide[0208] To a round bottom flask was added methyl 3,4,5-trimethoxybenzoate (11.3 g, 0.05 mmol), 80% hydrazine hydrate(40ml, 0.67mm0l), equipped with reflux stirrer at 92 ° C for 4 hours, when the reaction solution clear and clear, standing coldHowever, the precipitation of needle-like crystals, suction filtration, the collected filtrate directly re-use. Filter cake first washed with water, then acetone washing 2 times, tooTo the white crystal, i.e., 3,4,5-trimethoxybenzoyl hydrazide, 11. lg, yield 98.2%. |
92% | With hydrazine In methanol; water monomer Reflux; | |
92% | With hydrazine hydrate monohydrate In ethanol for 2h; Reflux; | 2.1.1.1. 3,4,5-trimethoxybenzohydrazide (4) To a solution of 1 (5.0 g, 22.1mmol) in absolute ethanol (60 mL), 21.4 mL (442 mmol) of hydrazine hydrate 64 % was added. The reaction mixture was kept under reflux for 2 hours, when TLC indicated the end of the reaction. Then, the media was poured into ice and the resulting precipitate was filtered out affording the 3,4,5-trimethoxybenzohydrazide (4) obtained as a white solid, in 92% yield, m.p. 166-168°C. The melting point, 1H NMR, 13C NMR and IR data were found to be in agreement with the previous report [30]. |
91.4% | With hydrazine | |
90% | With hydrazine hydrate monohydrate at 95℃; for 3h; | |
90% | With hydrazine hydrate monohydrate In ethanol for 14h; Reflux; | |
89% | With hydrazine hydrate monohydrate In methanol for 5h; Heating; | |
89% | With hydrazine monohydrate In ethanol for 12h; Reflux; | 2 2.2.2 3,4,5-Trimethoxybenzohydrazide (2a) A mixture of methyl 3,4,5-trimethoxybenzoate (0.45 g, 2 mmol) and hydrazine hydrate (55%, 0.64 g, 20 mmol) in 20 mL of ethanol was refluxed for 12 h. After completion of the reaction, the EtOH was evaporated under reduced pressure. Hexane was added into the crude mixture, and the obtained precipitate was filtered and washed with hexane to afford 2a as a white solid (0.4 g, 89%). 2a: FT-IR (KBr), ν (cm- 1): 1126, 1230, 1341, 1581, 3334; 1H NMR (CDCl3, 600 MHz), δ (ppm): 3.87 (3H, s), 3.88 (6H, s), 6.98 (2H, s), 7.54 (1H, s); 13C NMR (CDCl3, 600 MHz), δ (ppm): 56.3, 60.9, 104.3, 153.3. ESI-MS m/z: Calcd for C10H14N2O4 (M + Na)+: 249.0851, found: 249.0859. |
88% | With hydrazine monohydrate In methanol for 5h; Reflux; | General procedure for the preparation of acid hydrazides(18a-j) To a solution of an appropriate methyl esters17(a-j) (1.0 mmol) in 50 mL of methanol was added 99 %hydrazine hydrate (4.0 mmol) and the mixture was refluxedfor 5 h up to reaction completed (TLC). After completionof reaction, it was allowed to cool and the obtained solidwas washed with methanol. The crude products wererecrystallized from ethanol.3,4,5-Trimethoxybenzohydrazide (18a) White solid;Yield: 88 %; mp 162-164 °C; 1H NMR (DMSO-d6,400 MHz): δ 9.55 (1H, brs, -NH), 7.18 (2H, s, H-2, H-6),3.98 (2H, brs, -NH2), 3.83 (9H, s, 3 X O-CH3); 13C NMR(DMSO-d6, 125 MHz): δ 165.6 (C=O), 158.7 (C, C-3, C-5), 130.0 (C, C-4), 128.4 (C, C-1), 127.5 (CH, C-2, C-6),59.1 (O-CH3), 56.3 (O-CH3); for C10H14N2O4 MS (ESI)(m/z) 227 [M + H]+. |
86.4% | With hydrazine hydrate monohydrate In methanol for 5h; Heating; | |
85% | With hydrazine monohydrate Reflux; | 2 In a 1000 mL / 1 mouth reaction flask, the ester obtained in the first step was placed (48g, 0.212 mol), with a solution of 99% hydrazine hydrate (N2H4.H2O) (77.6g, 1.54mol) and an organic solvent which may be ethanol, ethyl acetate, dichloromethane, acetone, methanol (200 mL). The mixture was refluxed for 1 to 5h and maintained overnight under magnetic stirring only at a temperature between 0 and 50°C. The solid obtained was filtered and recrystallized in methanol to obtain the 3,4,5-trimethoxyphenyl-hydrazide as white crystals with a yield of 85%; mp: 162-163°C (lit. mp 168°C). NMR 1H (CDCl3): 3.80 (s, 3H, OCH3), 3.90 (s, 6H, OCH3), 7.18 (s, 2H, Ar), 9.55 (NH). |
85% | With hydrazine hydrate monohydrate In ethanol for 18h; Reflux; | |
83% | With hydrazine monohydrate In ethanol for 8h; Reflux; | |
83% | With hydrazine hydrate monohydrate In ethanol for 42h; Reflux; | Preparation of 3,4,5-trimethoxybenzohydrazide (10) [2] Excess of hydrazine hydrate 100% (0.850 mol, 42.551 g, 3.269 equiv.) was added portionwise to a stirred solution of the ester (9) (0.260mol, 58.820 g) in absolute ethanol (200 mL). The mixture was then gently refluxed for 42 h. The solvent and the excess of hydrazine weredistilled off and the remaining residue was rinsed with water, then the crude product was allowed to crystallize from saturated ethanolic solutionat 70C, only the first crop of crystalline hydrazide was collected and dried at 130 °C for 3 h. Yield: 49 g (83%), m.p= 166 C (lit 168°C [2]). IR:3323-3201 cm-1 (NHNH2), 1702 cm-1 (C=O). |
80% | With hydrazine hydrate monohydrate In ethanol | |
75% | With hydrazine hydrate monohydrate In ethanol for 24h; Heating; | |
70% | With hydrazine hydrate monohydrate In methanol at 65℃; for 6h; | 1. Synthesis of 3,4,5-trimethoxyhydrazide (4) A mixture of 5 mmol of metA mixture of 5 mmol of methyl ester 3 and 25 mmol of hydrazine hydrate (98%) in 5 ml of methanol was refluxed for 6 h. After cooling a white precipitate of the desired hydrazide 4 was formed and filtered off. Yield 70%, m.p.160°Chyl ester 3 and 25 mmol of hydrazine hydrate (98%) in 5 ml of methanol was refluxed for 6 h. After cooling a white precipitate of the desired hydrazide 4 was formed and filtered off. Yield 70%, m.p.160°C [lit.[2] 162-164 °C]. |
68% | With hydrazine hydrate monohydrate Ambient temperature; | |
68% | With hydrazine hydrate monohydrate In methanol for 6h; Reflux; | |
67% | With hydrazine hydrate monohydrate In ethanol for 8h; Reflux; | |
With methanol; hydrazine hydrate monohydrate | ||
With hydrazine hydrate monohydrate | ||
With hydrazine hydrate monohydrate | ||
With hydrazine hydrate monohydrate In methanol | ||
With hydrazine hydrate monohydrate Reflux; | ||
With sulfuryl dichloride; hydrazine hydrate monohydrate Reflux; | ||
With hydrazine hydrate monohydrate In methanol at 20℃; Reflux; | 4.1.1. General procedure for the synthesis and purification of 3,4,5-trimethoxybenzohydrazide [21] The 3,4,5-trimethoxybenzohydrazide was obtained from amixture of gallic acid (6 mmol), dimethyl sulphate (28 mmol),anhydrous K2CO3 (26 mmol) and tetrabutylammonium iodide(TBAI) (0.1 g) in acetone (30 mL) [21]. The mixture was refluxed for12 h, after the precipitate was filtered and washed with acetone.The ester obtained (6 mmol) was treated with a solution of 99%N2H4 (4.4 mmol) in methanol (20 mL) and refluxed for 5 h, and thenkept at room temperature overnight. The solid obtained wasfiltered and recrystallized from hot methanol to afford the 3,4,5-trimethoxybenzohydrazide (80%). | |
With hydrazine hydrate monohydrate In ethanol Reflux; | ||
With hydrazine hydrate monohydrate In methanol for 8h; Reflux; | General Procedure for the Synthesis of Acid Hydrazides (3a-t) General procedure: To a solution of methyl ester of aromatic carboxylic acid 2 (0.1 mol) in methanol (30 mL), hydrazine hydrate (0.2 mol) was added drop wise with stirring. The resulting mixture was allowed to reflux for 8 h. After the completion of the reaction as monitored by TLC, the excess methanol was distilled off under reduced pressure. The resulting acid hydrazide 3 was washed with cold water, dried and recrystallized from ethanol. | |
With hydrazine hydrate monohydrate In methanol at 70℃; for 2h; Microwave irradiation; | ||
22.62 g | With hydrazine hydrate monohydrate In methanol for 15h; Reflux; | |
Stage #1: 3,4,5-trimethoxybenzoic acid methyl ester In methanol at 0℃; for 0.166667h; Stage #2: With hydrazine monohydrate In methanol for 8h; Reflux; | Step 2. General Procedure for Preparation of the Benzoyl Hydrazines General procedure: A mixture of methyl benzoates (15.0 mmol), CH3OH (30.0 mL) wereplaced in a 100mL round-bottomed flask equipped with a magnetic stirrer.Stirring for 10 minutes in 0 °C. Then hydrazine hydrate (4.0 eq.) was added to the flask. Afterword the mixture was stirred under reflux 8 h, the reaction system was concentrated to remove CH3OH and most of hydrazine hydrate. After cooling, the contents were added petroleum-ether (50 mL) by stirring, then the white solids would be separated, washed with water and dried under vacuum. The yield was 65%~80%. | |
With hydrazine hydrate monohydrate at 80℃; for 5h; | 10.1 1) In a 100 ml round bottom flask,19.44 g (80.0 mm mol) of methyl 3,4,5-trimethoxybenzoate was added,And hydrazine hydrate 30ml (excess) at 80 for 5h,After the reaction was completely cooled, the solid was precipitated at low temperature,Filter,Dried to give 3,4,5-trimethoxybenzohydrazide. | |
With hydrazine monohydrate In ethanol | ||
With hydrazine hydrate monohydrate In ethanol Reflux; | ||
With hydrazine monohydrate In ethanol Reflux; | ||
With hydrazine hydrate monohydrate In ethanol | ||
With hydrazine hydrate monohydrate In ethanol for 6h; Reflux; | ||
With hydrazine hydrate monohydrate for 4h; Reflux; | 4.2.1. General procedure for the synthesis of hydrazides 2 General procedure: Hydrazides 2 were obtained in reaction of methyl esters 1 (1 mmol), which synthesized from corresponding acids [61], and hydrazine monohydrate (6 mmol) by heating under reflux for 4 h [62]. | |
With hydrazine hydrate monohydrate In methanol at 80℃; for 4h; | preparation of intermediate 2 General procedure: At the 250 cm3double-mouth bottle, 13.5 mmol of themethyl benzoate derivatives was added to 100 cm3of methanol,added 6.75 cm3of hydrazine hydrate (108 mmol) tothe reaction mixture slowly. After that warming to 80 °Cand reflux for 4 h until the reaction was completed, thenconcentrated under reducing pressure to remove methanol,filtering and drying to get white solid 2. | |
With hydrazine hydrate monohydrate In ethanol Reflux; | ||
With hydrazine hydrate monohydrate In methanol | ||
With hydrazine hydrate monohydrate In ethanol at 80℃; for 6h; | General procedure: The crude methyl ester (1 mmol) was dissolved in anhydrous methanol and hydrazine hydrate (1.5 mmol) was added. Then, the mixture was refluxed for about 6 h. After completion of the reaction as monitored by TLC, the mixture was cooled to room temperature. Upon cooling the precipitate, it was filtered and dried to give the aryl hydrazide product 3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydrogencarbonate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrazine hydrate monohydrate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 5 - 20℃; | Method 2: Compound 2 (1 g, 4.71 mmol)was dissolved in THF (10 mL) containing DIPEA(5.65 mmol) and cooled to 5°C. To the above solution,HATU (1.79 g, 4.71 mmol) was added in fve portionsand stirred at room temperature for 4 h. Water (20mL) was added to the reaction contents and wastaken in dichloromethane (50 mL), the organic layerwas separated, washed with water (2 X 15 mL) andthen with brine solution. The dichloromethane layerwas dried over Na2SO4, fltered and concentratedunder reduced pressure to isolate compound 3. Yield:95%. |
85% | With hydrazine hydrate monohydrate Reflux; | 2 Obtaining Hydrazide: [0098] In a 1000 mL/1 mouth reaction flask, the ester obtained in the first step was placed (48 g, 0.212 mol), with a solution of 99% hydrazine hydrate (N2H4.H2O) (77.6 g, 1.54 mol) and an organic solvent which may be ethanol, ethyl acetate, dichloromethane, acetone, methanol (200 mL). The mixture was refluxed for 1 to 5 h and maintained overnight under magnetic stirring only at a temperature between 0 and 50° C. The solid obtained was filtered and recrystallized in methanol to obtain the 3,4,5-trimethoxyphenyl-hydrazide as white crystals with a yield of 85%; mp: 162-163° C. (lit. mp 168° C.). NMR 1H (CDCl3): 3.80 (s, 3H, OCH3), 3.90 (s, 6H, OCH3), 7.18 (s, 2H, Ar), 9.55 (NH). |
Multi-step reaction with 3 steps 1.1: oxalyl chloride / N,N-dimethylformamide / CH2Cl2 2.1: Na 2.2: 83 percent / methanol / 5 h / 20 °C 3.1: 75 percent / hydrazine hydrate / ethanol / 24 h / Heating |
Multi-step reaction with 2 steps 1: H2SO4 2: NH2NH2*H2O | ||
Multi-step reaction with 2 steps 1: 83 percent / H2SO4 2: 68 percent / 35percent aq. hydrazine / Ambient temperature | ||
Multi-step reaction with 2 steps 1: conc. H2SO4 / 20 h / Heating 2: H2NNH2*H2O / 6 h / Heating | ||
Multi-step reaction with 2 steps 1: thionyl chloride / 3 h / Reflux 2: hydrazine hydrate monohydrate / methanol / 6 h / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid / 4 h / Reflux 2: hydrazine monohydrate / ethanol / 8 h / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: hydrazine hydrate monohydrate / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid 2: hydrazine hydrate monohydrate / ethanol / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid 2: hydrazine hydrate monohydrate / ethanol | ||
Multi-step reaction with 2 steps 1: sulfuric acid / 8 h / Reflux 2: hydrazine monohydrate / ethanol / 6.5 h / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid 2: hydrazine hydrate monohydrate / ethanol | ||
Multi-step reaction with 2 steps 1: sulfuryl dichloride / Reflux 2: sulfuryl dichloride; hydrazine hydrate monohydrate / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: hydrazine hydrate monohydrate / ethanol / Reflux | ||
Stage #1: Eudesmic acid In methanol Acidic conditions; Stage #2: With hydrazine In methanol | ||
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: hydrazine hydrate monohydrate / ethanol / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid / 10 h / Reflux 2: hydrazine hydrate monohydrate / ethanol / 8 h / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid / 3 h / 70 °C 2: H4N2*5H2O / ethanol / 6 h / 70 °C | ||
Multi-step reaction with 2 steps 1: sulfuric acid / 6 h / Reflux 2: hydrazine monohydrate / methanol / 5 h / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: hydrazine hydrate monohydrate / ethanol / Reflux | ||
Multi-step reaction with 2 steps 1: glycerol-based sulfonic acid functionalized carbon catalyst / 6 h / Reflux; Green chemistry 2: hydrazine hydrate monohydrate / methanol / 8 h / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid / 12 h / Reflux 2: hydrazine hydrate monohydrate / ethanol / 6 h / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid / water monomer / 0.45 h / 70 °C / Microwave irradiation 2: hydrazine hydrate monohydrate / methanol / 2 h / 70 °C / Microwave irradiation | ||
Multi-step reaction with 2 steps 1: sulfuric acid / water monomer / 12 h / Reflux 2: hydrazine hydrate monohydrate / methanol / 15 h / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid / 10 h / Reflux 2: hydrazine hydrate monohydrate / ethanol / 10 h / Reflux | ||
Multi-step reaction with 2 steps 1.1: 0.17 h / 0 °C 1.2: 6 h / Reflux 2.1: methanol / 0.17 h / 0 °C 2.2: 8 h / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: hydrazine / water monomer; methanol / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: hydrazine hydrate monohydrate / ethanol / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid / Inert atmosphere 2: hydrazine / ethanol / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: hydrazine hydrate monohydrate / ethanol / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: hydrazine hydrate monohydrate / ethanol / Reflux | ||
Stage #1: Eudesmic acid at 210℃; for 2h; Stage #2: With sulfuric acid In methanol Reflux; Stage #3: With hydrazine hydrate monohydrate In ethanol Reflux; | ||
220.7 mg | With CuO/Cr2O3; hydrazine hydrate monohydrate at 98 - 100℃; | 3 Example 3 212 g of 3,4,5-trimethoxybenzoic acid, 320 g of hydrazine hydrate having a content of 99%, and 42 g of CuO/Cr 2 O 3 composite catalyst were placed in a stirring, thermometer,In the four-necked flask of the rectification column, the stirring is started, and the heating is heated to reflux. When the steam enters the rectification column, water vapor is collected at the column top temperature of 98 ° C to 100 ° C, and reacted at the reflux temperature for 4 to 6 hours. The reaction is terminated after the condensate is discharged from the top of the column.The hydrazine hydrate remaining in the flask was distilled off by vacuum distillation, and the hydrazine hydrate was completely distilled off, and then the solid substance in the flask was sufficiently dissolved by adding an appropriate amount of pure water, and then the solution was poured out, and the CuO/Cr2O3 composite catalyst was recovered by suction filtration, and the filtrate was filtrated. Transfer to a distillation flask, evaporate and concentrate under reduced pressure, and remove water to obtain crude 3,4,5-trimethoxybenzoyl hydrazide.After washing with absolute ethanol and drying, 220.7 g of a 3,4,5-trimethoxybenzohydrazide product was obtained. |
With hydrazine monohydrate at 98 - 100℃; Molecular sieve; | 3 212 g of 3,4,5-trimethoxybenzoic acid, 324 g of hydrazine hydrate having a content of 98%, and 42 g of ZSM-5 acid zeolite molecular sieve were placed with stirring,In the four-necked flask of the thermometer and the rectification column, the stirring is started, and the heating is heated to reflux, and when the steam enters the rectification column,Water vapor is collected at a column top temperature of 98 ° C to 100 ° C, and reacted at a reflux temperature for 4 to 6 hours. When the top of the rectification column is free of condensed water, the reaction is terminated, and the remaining hydrazine hydrate in the flask is distilled off by vacuum distillation, and the hydrazine hydrate is completely distilled off, and the solid substance in the flask is fully dissolved by adding an appropriate amount of pure water, and then The solution was poured out, and the ZSM-5 acid zeolite molecular sieve catalyst was recovered by vacuum filtration. The filter cake was washed with an appropriate amount of pure water, and the filtrate was transferred to a distillation flask and concentrated under reduced pressure.After removing water, a crude 3,4,5-trimethoxybenzoyl hydrazide is obtained, which is then washed with absolute ethanol.After drying, 220.2 g of a 3,4,5-trimethoxybenzoylhydrazine finished product was obtained. | |
220.6 g | With hydrazine hydrate monohydrate; dicyclohexyl-carbodiimide at 95 - 100℃; | 3 212 g of 3,4,5-trimethoxybenzoic acid, 324 g of hydrazine hydrate having a content of 98% and 63 g of dicyclohexylcarbodiimide were placed in a four-necked flask equipped with a stirring, a thermometer and a rectification column. , stirring is started, heating is heated to reflux, and when steam enters the rectification column, water vapor is collected at a column top temperature of 95 ° C to 100 ° C, and reacted at a reflux temperature for 4 to 6 hours, when the top of the rectification column is not condensed.After the water is discharged, the reaction is terminated, and the remaining hydrazine hydrate and the dicyclohexylcarbodiimide catalyst are distilled off by distillation under reduced pressure, and the hydrazine hydrate and dicyclohexylcarbodiimide are completely distilled off, and then the flask is placed therein. The solid matter was dissolved in pure water, filtered, recrystallized and dried to give 220.6 g of 3,4,5-trimethoxybenzoylhydrazine. |
220.5 g | With hydrazine monohydrate at 98 - 100℃; Molecular sieve; Reflux; | 3 Example 3 212 g of 3,4,5-trimethoxybenzoic acid,Hydrazine hydrate 320g in a content of 99% and 42g of mordenite molecular sieve in a beltStirring,thermometer,In the four-necked flask of the rectification column,Turn on the agitation,Heating to reflux,When the steam enters the rectification column,Water vapor is produced at a column top temperature of 98 ° C to 100 ° C.React at reflux temperature for 4 to 6 hours,When the top of the distillation column has no condensed water flowing out, the reaction is terminated.The remaining hydrazine hydrate in the flask was distilled off by distillation under reduced pressure,After the hydrazine hydrate is completely distilled off, an appropriate amount of pure water is added to fully dissolve the solid matter in the flask.Then pour the solution out,The mordenite molecular sieve catalyst is recovered by vacuum suction filtration,The filtrate was transferred to a distillation flask and concentrated under reduced pressure.After removing water, a crude 3,4,5-trimethoxybenzoyl hydrazide is obtained.Wash with anhydrous ethanol,After drying, 220.5 g of a 3,4,5-trimethoxybenzoylhydrazine finished product was obtained. |
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: hydrazine hydrate monohydrate / ethanol / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid / 7 h / 80 °C 2: hydrazine / methanol / 7 h / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: hydrazine hydrate monohydrate / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid 2: hydrazine hydrate monohydrate / ethanol | ||
Multi-step reaction with 3 steps 1: thionyl chloride / 2 h / Reflux 2: methanol / 2 h / 20 °C 3: hydrazine hydrate monohydrate / ethanol / 42 h / Reflux | ||
Stage #1: Eudesmic acid With sulfuric acid In ethanol Reflux; Stage #2: With hydrazine hydrate monohydrate In ethanol Reflux; | ||
Multi-step reaction with 2 steps 1: sulfuric acid / ethanol / Reflux 2: H4N2*5H2O / ethanol / Reflux | ||
Multi-step reaction with 2 steps 1: thionyl chloride; 1,2,3-Benzotriazole / dichloromethane / 20 °C 2: hydrazine / acetonitrile / 0.25 h / 20 °C | ||
Multi-step reaction with 2 steps 1: sulfuric acid / 8 h / Reflux 2: hydrazine hydrate monohydrate / ethanol / 14 h / Reflux | ||
Multi-step reaction with 2 steps 1: sulfuric acid 2: hydrazine hydrate monohydrate / methanol | ||
Multi-step reaction with 2 steps 1: sulfuric acid / 6 h / 0 - 80 °C 2: hydrazine hydrate monohydrate / ethanol / 6 h / 80 °C | ||
Multi-step reaction with 2 steps 1: sulfuric acid / 8 h / Reflux 2: hydrazine hydrate monohydrate / ethanol / 8 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 75 percent / 1 h / Heating 2: 75 percent / 5percent NaOH / H2O / 4 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; for 2h;Reflux; | General procedure: The hydrazones were synthesized from the 3,4,5-trimethoxybenzohydrazide (2 mmol) or benzohydrazide(2 mmol) and the appropriate aldehydes (2 mmol) in methanol(15 mL) and refluxed for 2 h. After cooling, the crude product wascollected by filtration, washed and recrystallized from hot ethanolto give white solids [11]. Hydrazones 10, 22, 26 and 34 are novelcompounds, which were recently patented by our group [25]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With potassium carbonate In butan-1-ol at 160℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In ethanol; for 1h;Reflux; | General procedure: Aromatic/heteroaromatic aldehydes a-l(1.0 mmol) was added to ethanol (2 mL) containingcompound 3 (100 mg, 0.40 mmol) and heated toreux point for 1h. The solids obtained was flteredand slurred with ethanol (1mL) followed by n-Hexaneto get the hydrazones 4a-l . |
50% | In methanol; for 2h;Reflux; | General procedure: The hydrazones were prepared by condensation of hydrazide (2 mmol) and the appropriate aldehyde (2 mmol), in methanol (15 mL) under reflux for 2h. After cooling, the crude product was collected by filtration, washed and recrystallized from hot ethanol to give a white solid.18 |
In methanol; for 2h;Reflux; | General procedure: The hydrazones were synthesized from the 3,4,5-trimethoxybenzohydrazide (2 mmol) or benzohydrazide(2 mmol) and the appropriate aldehydes (2 mmol) in methanol(15 mL) and refluxed for 2 h. After cooling, the crude product wascollected by filtration, washed and recrystallized from hot ethanolto give white solids [11]. Hydrazones 10, 22, 26 and 34 are novelcompounds, which were recently patented by our group [25]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.4% | With trichlorophosphate for 6h; Reflux; | 2. General experimental procedure for synthesis of compound 7 General procedure: A mixture of aryl acid hydrazide (10mmol), chloroacetic acid (10mmol) and POCl3 (7mL) was heated under reflux for 6h. The excess POCl3 was removed under reduced pressure and the residue was poured onto crushed ice. The resuting precipitate was filtered, washed with saturated sodium bicarbonate solution and then with water, dried and recrystallized from ethanol/water to afford compound 7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In methanol; for 2h;Reflux; | General procedure: The hydrazones were synthesized from the 3,4,5-trimethoxybenzohydrazide (2 mmol) or benzohydrazide(2 mmol) and the appropriate aldehydes (2 mmol) in methanol(15 mL) and refluxed for 2 h. After cooling, the crude product wascollected by filtration, washed and recrystallized from hot ethanolto give white solids [11]. Hydrazones 10, 22, 26 and 34 are novelcompounds, which were recently patented by our group [25]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In methanol; for 2h;Reflux; | General procedure: The hydrazones were synthesized from the 3,4,5-trimethoxybenzohydrazide (2 mmol) or benzohydrazide(2 mmol) and the appropriate aldehydes (2 mmol) in methanol(15 mL) and refluxed for 2 h. After cooling, the crude product wascollected by filtration, washed and recrystallized from hot ethanolto give white solids [11]. Hydrazones 10, 22, 26 and 34 are novelcompounds, which were recently patented by our group [25]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With trifluoroacetic acid; In chloroform; for 4h;Reflux; | General procedure: Aldehyde (1.5 mmol, 1 eq.) and the corresponding hydrazide (1.5 mmol/3 mmol/4.5 mmol, 1eq.) were dissolved in chloroform (50 mL). Trifluoroacetic acid (30 muL) was added, then heated to reflux for 4 h and left to cool to room temperature. The resulted solid was filtered, washed with cold diethyl ether and further used without any other purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With trifluoroacetic acid; In chloroform; for 4h;Reflux; Inert atmosphere; | General procedure: Aldehyde 2 (1 mmol) and the corresponding hydrazide 3 (1mmol) were dissolved in CHCl3 (10 mL). Trifluoroacetic acid (a few drops) was added and the resulted solution heated to reflux for 4 h. After cooling, the solvent was removed in vacuum and the residue was washed with cold diethyl ether. The product was further used without any other purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With acetic acid In ethanol for 4h; Reflux; | General procedure for the synthesis of N'-((1-(substituted)-1H-indol-3-yl)methylene)hydrazides (18a-v) General procedure: Indole-3-aldehyde 16 (1 mmol) and the correspondingalkyl/aryl acid hydrazide 17 (1.05 mmol) were refluxed in ethanol (5 mL) in the presence of glacial acetic acid(0.3 mL) for 4 h. On cooling the reaction mixture to roomtemperature, the crude product was precipitated, filteredand dried. Further recrystallization of the crude products inethanol allowed to obtain pure products in 85-95 % yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol for 1h; Reflux; | 5.1.1. General procedure for the target compounds 5~6 General procedure: To a 100 mL round-bottom flask, 3,4,5-trimethoxybenzoic acid(10.6 g, 50 mmol), 1 mL of concentrated sulfuric acid and 30 mL ofethanol were added gradually. The resulting mixture was stirred atreflux for 12 h and was then concentrated on a rotary evaporator.The crude product obtained was poured into 50 mL of water andextracted with ethyl acetate. The combined ethyl acetate extractswere washed with water, dried with anhydrous magnesium sulfatefiltered off by suction and the solvent was evaporated to give crudeethyl 3,4,5-trimethoxybenzoate, which and hydrazine hydrate(7.5 g, 150 mmol, 60%) in 50 mL of ethanol was heated under refluxfor 6 h. Excess ethanol was distilled out and the contents wereallowed to cool. The solid product obtained was filtered, washedthoroughly with water, and dried to give 3,4,5-trimethoxybenzohydrazide in total yield of 83%, which was usedfor the next reactions without further purification. A solution of3,4,5-trimethoxybenzohydrazide (3.39 g, 15 mmol) and appropriateisothiocyanatobenzenes (15 mmol) in ethanol (40 mL) washeated at reflux for 1 h, then cooled at room temperature. Thesuspensionwas filtered, and the solidwaswashed with ethanol anddried to give the intermediate hydrazinecarbothioamide as whitesolid. Then 1 N NaOH (30 mL) was added to this solid and themixture was heated at reflux for 1 h. The resulting solution wascooled at room temperature and acidified to pH 5e6 with 1 M HCl.The precipitatewas filtered,washed withwater, and dried to obtainthe title compounds as white solid. | |
In ethanol for 4h; Reflux; | Synthesis: 4-(4-Methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole-3-thiol (4): 4-Methoxyphenyl isothiocyanate (1.65gm,10 mmol) was added to a solution of 3,4,5-trimethoxybenzohydrazide (2.263 g, 10 mmol) in ethanol(30 mL), the mixture was then subjected to reflux conditionsfor 4 h then was cooled at room temperature. The formedsolid was collected by filtration and washed with ethanol and derided. | |
In ethanol Reflux; |
In ethanol for 5h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In butan-1-ol Heating; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In butan-1-ol Heating; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: butan-1-ol / Heating; Microwave irradiation 2: hydrazine hydrate; iron(III) chloride hexahydrate; pyrographite / methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In ethanol; for 1h;Reflux; | General procedure: Aromatic/heteroaromatic aldehydes a-l(1.0 mmol) was added to ethanol (2 mL) containingcompound 3 (100 mg, 0.40 mmol) and heated toreux point for 1h. The solids obtained was flteredand slurred with ethanol (1mL) followed by n-Hexaneto get the hydrazones 4a-l . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In ethanol for 1h; Reflux; | Preparation of Hydrazone derivatives 4a-l General procedure: Aromatic/heteroaromatic aldehydes a-l(1.0 mmol) was added to ethanol (2 mL) containingcompound 3 (100 mg, 0.40 mmol) and heated toreux point for 1h. The solids obtained was flteredand slurred with ethanol (1mL) followed by n-Hexaneto get the hydrazones 4a-l . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In ethanol; for 1.0h;Reflux; | General procedure: Aromatic/heteroaromatic aldehydes a-l(1.0 mmol) was added to ethanol (2 mL) containingcompound 3 (100 mg, 0.40 mmol) and heated toreux point for 1h. The solids obtained was flteredand slurred with ethanol (1mL) followed by n-Hexaneto get the hydrazones 4a-l . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In ethanol for 1h; Reflux; | Preparation of Hydrazone derivatives 4a-l General procedure: Aromatic/heteroaromatic aldehydes a-l(1.0 mmol) was added to ethanol (2 mL) containingcompound 3 (100 mg, 0.40 mmol) and heated toreux point for 1h. The solids obtained was flteredand slurred with ethanol (1mL) followed by n-Hexaneto get the hydrazones 4a-l . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 80℃; for 3h; | General procedure: 8-Methoxyquinoline-2-carbaldehyde (25, 0.534 mmol) was refluxedwith various substituted acylhydrazines (0.587 mmol, 1.1 eq) in ethanol(5-10 mL) to get acyl hydrazides of 8-hydroxyquinoline. After completionof reaction, quinoline acyl hydrazides were found as precipitateson cooling to -15 C. Precipitates were washed with coldethanol and dried under vacuum. These acyl hydrazides were used directlyfor one pot synthesis of 2,5-disubstituted-1,3,4-oxadiazole usingiodine/K2CO3 catalysed oxidative cyclization. To the acyl hydrazides(1.0 eq) in DMSO (5-10 mL), K2CO3 (3.0 eq) and iodine (1.2 eq) wereadded in sequence and refluxed at 110 C. After the completion, thereaction mixture was cooled and saturated solution of sodium thiosulfatewas added. The precipitates were collected and dried under highvacuum to get the respective compounds (33-50). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With hydrogenchloride; In ethanol; at 20℃; | General procedure: To a solution of hydrazide (4, or 5 or 6) (0.2 g, 0.88 mmol) in absolute ethanol (7 mL) containing one drop of 37percent hydrochloric acid, 0.88 mmol of corresponding alde-hyde derivative was added. The mixture was stirred at room temperature until TLC indicated the end of the reaction. The mixture was poured into ice and the precipitate was filtered out and dried. Flash chromatographic column was performed for purification of the final compounds, when necessary. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In ethanol; for 5.0h;Reflux; | General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In 1,4-dioxane at 80℃; for 9h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With acetic acid In ethanol at 20℃; | General experimental procedure for the preparationof (E)-N'-(pyridin-3-ylmethylene) benzohydrazides, 3a-y General procedure: Glacial acetic acid (0.2 mL) was added to a stirredsolution of nicotinaldehyde 1a (1.0 mmol), benzohydrazide 2a (1.0 mmol) in absolute ethanol (3 mL) at RT and the contents were stirred at the same temperature. After completion of the reaction (TLC, 1h), the reaction mixture was filtered through Whatman filter paper and compound wasrecrystallized from ethanol to afford (E)-N'-(pyridin-3-ylmethylene)benzohydrazide 3a as colourless solid.The compounds 3b-y were prepared by the reaction ofnicotinaldehydes 1a-b with benzohydrazides 2a-eunder above conditions. All the prepare compoundsare unknown and well characterized by spectral data. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol at 80℃; | General Procedure for the Synthesis of Benzimidazole Conjugated Oxadiazole Derivatives (4a-q) General procedure: A mixture of the benzohydrazide 2 (0.2 mmol) and aldehydes3 (1 equiv.) in absolute ethanol (4 mL) was stirred at80 °C for 4-9 h. After cooling down to room temperature, theexcess solvent was evaporated under reduced pressure to obtainthe intermediate imines which were used for the next stepwithout further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol at 80℃; | General Procedure for the Synthesis of Benzimidazole Conjugated Oxadiazole Derivatives (4a-q) General procedure: A mixture of the benzohydrazide 2 (0.2 mmol) and aldehydes3 (1 equiv.) in absolute ethanol (4 mL) was stirred at80 °C for 4-9 h. After cooling down to room temperature, theexcess solvent was evaporated under reduced pressure to obtainthe intermediate imines which were used for the next stepwithout further purification. |
Tags: 3291-03-0 synthesis path| 3291-03-0 SDS| 3291-03-0 COA| 3291-03-0 purity| 3291-03-0 application| 3291-03-0 NMR| 3291-03-0 COA| 3291-03-0 structure
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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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