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CAS No. : | 16420-13-6 | MDL No. : | MFCD00004919 |
Formula : | C3H6ClNS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PHWISQNXPLXQRU-UHFFFAOYSA-N |
M.W : | 123.60 | Pubchem ID : | 27871 |
Synonyms : |
|
Num. heavy atoms : | 6 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.67 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 32.02 |
TPSA : | 35.33 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.07 cm/s |
Log Po/w (iLOGP) : | 1.82 |
Log Po/w (XLOGP3) : | 1.38 |
Log Po/w (WLOGP) : | 1.07 |
Log Po/w (MLOGP) : | 0.6 |
Log Po/w (SILICOS-IT) : | 1.33 |
Consensus Log Po/w : | 1.24 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.41 |
Solubility : | 4.81 mg/ml ; 0.0389 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.73 |
Solubility : | 2.33 mg/ml ; 0.0188 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.71 |
Solubility : | 23.9 mg/ml ; 0.193 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.79 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 3261 |
Hazard Statements: | H302-H314-H317 | Packing Group: | Ⅱ |
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 |
---|---|---|
88% | at 60℃; for 0.166667 h; Microwave irradiation; Green chemistry | Add 1 mmol of o-phenylenediamine to the reaction vessel.Add 0.05 mmol of cuprous iodide sequentially.1 mmol of sodium hydroxide, N,N-dimethylaminothioformyl chloride 2.5 mmol,3 ml pyridine.Heated to 60 ° C at 120 W in a microwave reactorContinuous reaction for 10 min.After the reaction is completed, it is cooled to room temperature.Concentrated under reduced pressure,The product is purified by column chromatography.A white solid was obtained in 88percent yield. |
87% | With iron(III) chloride; caesium carbonate In tetrahydrofuran at 60℃; for 5 h; Green chemistry | Add 1 mmol of o-phenylenediamine to the reaction vessel.Add 0.1 mmol of ferric chloride in sequence,Cesium carbonate 1 mmol,N,N-dimethylaminothioformyl chloride 2.5 mmol,3 ml of tetrahydrofuran. Heat to 60 ° C for 5 h. After the reaction is completed, it is cooled to room temperature.Concentrated under reduced pressure, the product was purified by column chromatography.A white solid was obtained in a yield of 87percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,4-diaza-bicyclo[2.2.2]octane; at 0 - 20℃; for 16h;Inert atmosphere; | <strong>[5870-38-2]2,5-dihydroxyterephthalic acid diethyl ester</strong> (10 g, 39.00 mmol) and DABCO (18 g, 157 mmol) were dissolved in DMA (100 mL) under nitrogen atmosphere and the reaction temperature was adjusted to 0 C And cooled. To this is added dimethyl thiocarbamoyl chloride (19 g, 157 mmol) dissolved in 50 mL of DMA dropwise. The mixture was stirred at room temperature for 16 hours. The obtained white precipitate was filtered, washed with a large amount of water, and dried under vacuum to synthesize 2,5-bis (dimethylthiocarbamoyloxy) terephthalic acid diethyl ester. The synthesized 2,5-bis (dimethylthiocarbamoyloxy) terephthalic acid diethyl ester was heated in a nitrogen atmosphere for 1 hour to a temperature range of 220-230 C. The resulting brownish compound was cooled to 70 C and ethanol Lt; / RTI & gt; The pale brown crystals obtained by cooling to room temperature are filtered to obtain 2,5-bis (dimethylthiocarbamoylsulfanyl) terephthalic acid diethyl ester. To the 1.3 M KOH solution prepared by mixing the above 2,5-bis (dimethylthiocarbamoylsulfanyl) terephthalic acid diethyl ester compound (1.3 g, 3.03 mmol) in a 1: 1 volume ratio of ethanol and water, For 3 hours. The resulting reaction was cooled in an ice bath and HCl solution (15 mL) was added thereto to obtain a yellow compound of formula (III). | |
With 1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl acetamide; at 0 - 20℃; for 16h;Inert atmosphere; | Under N2 protection,Will be 2g<strong>[5870-38-2]2,5-dihydroxy-1,4-benzenedicarboxylic acid diethyl ester</strong> with3.6 g of triethylene diamine (DABCO) was dissolved in 20 mLDried N, N-dimethylacetamide (DMA), cooled to 0 C in an ice bath;Then, 10 mL of the solution was dissolved under N2N, N-dimethylthioformyl chlorideThe DMA solution was slowly added dropwise to the above solution to keep the reaction temperature at 0 C;The mixture was then stirred at room temperature for 16 h to give a white precipitate which was filtered and washed with water, dried under vacuum and stored. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.8% | With dmap; triethylamine; In dichloromethane;Heating / reflux; | A mixture of <strong>[82380-18-5]2-fluoro-4-hydroxy benzonitrile</strong> (10 g, 0.0729 mol), DMAP (900 mg, 0.00729 mol), triethylamine (30 ml, 0.218 mol) and dimethylthiocarbamoyl chloride (11 g, 0.0875 mol) in dry dichloromethane (200 ml) was stirred at reflux under nitrogen atmosphere overnight. The reaction mixture was quenched with water and extracted with dichloromethane. The organic layer was washed with water, brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was triturated with pet ether. The product was filtered and dried under vacuum to give the sub-title compound (14 g, 85.8%) as yellow solid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | In tetrahydrofuran; water; at 0 - 20℃; for 0.166667h; | O- (L-BENZOTHIEN-4-VL)-DIMETHYLTHIOCARBAMATE A solution OF N, N-DIMETHYLTHIOCARBAMOYL chloride (4.55g, 36.6 mmol, 1.1 eq) in THF (10 ML) was added to a cooled solution (0C) of <strong>[3610-02-4]4-hydroxybenzothiophene</strong> (5 g, 33.2 mmol, 1 eq) and potassium hydroxide (2.05 g, 36.6 mmol, 1. 1 eq) in water (25 ml) at a rate such that the temperature did not exceed 10C. The reaction was stirred at room temperature for 10 minutes then extracted with ethyl acetate (3 x 50 ml). The combined organic extracts were washed successively with 2N NAOH (50 ml), water (50 ml), 2N HCl (50 ml) and brine (50 ml), then dried (MGS04) and the solvent removed in vacuo to give the crude product which was purified by flash chromatography in dichloromethane to give 4.33 g, 55% yield of title compound as a colourless solid; ON (300 MHz, CDC13) 7.81-7. 75 (1H, m, ArH), 7.44-7. 34 (2H, m, ArH), 7.26-7. 23 (1H, m, ArH), 7.08-7. 06 (1H, m, ArH), 3.51 (3H, s, N (CH3) 2) and 3.44 (3H, s, N (CH3) 2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; In N-methyl-acetamide; | (a) O-(2-benzoyl-5-methoxyphenyl)dimethylthiocarbamate Sodium hydride (8.8 g, Aldrich) was added slowly to a solution of 2-hydroxy -4-methoxybenzophenone (50.0 g, Aldrich) in 300 ml of dimethylformamide. Hexamethylphosphoramide (43.0 g) was then added dropwise and stirred at room temperature for 2 hours. Dimethylthiocarbamoyl chloride (37.0 g, Aldrich) was added and stirred overnight at 50 C. The reaction mixture was poured into deionized water (300 mL) and extracted with a petroleum ether/chloroform (1:4) mixture. The organic layer was washed with 10% sodium hydroxide, brine and concentrated to give the title product as a yellow solid (40.0 g), mp 94-96 C. 1 H NMR was consistent with proposed structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride; In DMF (N,N-dimethyl-formamide); at 20℃; for 44h; | To a stirred suspension of 60% sodium hydride in mineral oil (0.93 mg, 23.5 mmol) in DMF (27 [ML)] at room temperature under nitrogen atmosphere was added dropwise a solution of 3, 4-dimethoxy-5-hydroxybenzoic acid methyl ester (5.0 g, 23.5 mmol) in DMF (6 mL), followed by the dropwise addition of a solution [OF DIMETHYLTHIOCARBAMOYL] chloride (2.9 g, 23.5 mmol) in DMF (4 mL}. The reaction mixture was stirred at room temperature under nitrogen for 44 h, then diluted with ether (600 mL), filtered through a pad of celite and the filtrate was washed with water (3 x 200 mL). The organic layer was dried (Na2S04), filtered and evaporated in vacuo to give [3-DIMETHYLTHIOCARBOMYLOXY-4,] 5-dimethoxybenzoic acid methyl ester (4.07 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 1,4-diaza-bicyclo[2.2.2]octane; In DMF (N,N-dimethyl-formamide); at 20℃; for 7h; | <strong>[392-04-1]methyl 4-fluorosalicylate</strong> (10.0 g, 58 mmol) and N,N-dimethylthiocarbamoyl chloride (9.6 g, 77 mmol) were dissolved in DMF (100 ml), and 1,4-diazabicyclo[2.2.2]octane (8.5 g, 75 mmol) was added thereto.. The reaction mixture was stirred at room temperature for 7 hrs.. The reaction mixture was combined with ethyl acetate and water.. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.. The solvent was evaporated.. The residue was subjected to a silica gel column chromatography.. The fractions eluted with ethyl acetate-hexane (1:5, v/v) were collected, concentrated and recrystallized from ethyl acetate-hexane to give the titled compound (12.1 g, 80 %) as white crystals. mp. 106.8-107.2 C1H-NMR (CDCl3) delta: 3.39 (3H, s), 3.46 (3H, s), 3.83 (3H, s), 6.87 (1H, m), 7.02 (1H, m), 8.03 (1H, m). IR(KBr): 2949, 1728, 1606, 1539, 1496, 1396, 1286, 1257, 1151, 1113, 1086 cm-1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; triethylamine; In 1,4-dioxane; at 100℃; | To a solution of methyl 3-(3-hydroxyphenyl) propionate (9.31 g, 51.7 mmol, 1.0 equiv.) in dioxane (100 mL), was added dimethylthiocarbamoyl chloride (7.66 g, 62.0 mmol, 1.2 equiv.), Et3N (14.4 mL, 103.4 mmol, 2.0 equiv.), and DMAP (0.63 g, 5.2 mmol, 0.1 equiv.). The resulting mixture was stirred and heated to 100 C. overnight. The solution slowly changed color from yellow to brown over time. To the reaction mixture diluted with EtOAc (150 mL), and it was sequentially washed with water, brine, and dried over Na2SO4. After removal of solvent, the crude product was purified by chromatography to afford 9.6 g of yellow oil. 1H NMR (400 MHz, CDCl3) delta ppm. 7.29 (t, 1H), 7.19 (d, 1H), 6.90 (d, 1H), 6.89 (s, 1H), 3.65 (s, 3H), 3.41 (s, 3H), 3.32 (s, 3H), 2.94 (t, 2H), 2.64 (t, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In tetrahydrofuran; water; toluene; | EXAMPLE 1 O-[3,5-bis(1,1-dimethylethyl)phenyl]dimethylcarbamothioate (1) STR30 Potassium bis (trimethylsilyl) amide (15% by weight in toluene, 260 ml, 0.169 moles) was added by syringe to a solution of 3,5-di-tert-butylphenol (34.8 g, 0.169 moles) in tetrahydrofuran (500 ml). After 30 minutes, a solution of dimethylthiocarbamoyl chloride (24.7 g, 0.20 moles) in tetrahydrofuran (50 ml) was added over 10 minutes. The reaction mixture was stirred at room temperature for 30 minutes, and then at 50 C. for 1.5 hours. After cooling to room temperature, the reaction mixture was poured into cold (0 C.) water (100 ml) containing potassium hydroxide (30 g). The mixture was extracted twice with 1000 ml of ethyl ether. The combined ethyl ether extracts were dried over sodium sulfate, filtered and concentrated with a rotary evaporator to give the crude product as a yellow oil. The title product was purified by chromatography on silica gel and used directly in Example 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 20 - 60℃; for 17h; | To a mixture of 4-hydroxy-2-methyl-thiazole-5-carboxylic acid ethyl ester (7.2 g, 37.4 mmol) and 1 ,8- diazabicyclo[5.4.0]undec-7-ene (1 1.2 ml, 74.8 mmol) in DMF (50 ml) is added N,N-dimethyl- carbamothioyl chloride (6.94 g, 56.1 mmol). The mixture is stirred at RT for 14 h and at 60 C for 3 h, poured onto water ( 00 ml) and extracted with EtOAc (3 x 50 ml). The combined organic layers are washed with water (2 x 50 ml), dried over sodium sulfate and concentrated. The residue is chromatographed (silica gel, 10% EtOAc/hexane) to give 4-(dimethyl-carbamothioyl)oxy-2-methyl- thiazole-5-carboxylic acid ethyl ester (5.7 g, 20.7 mmol, 55%). |
55% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 23 - 60℃; for 17h; | To a mixture of 4-hydroxy-2-methyl-thiazole-5-carboxylic acid ethyl ester (7.2 g, 37.4 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (11.2 ml, 74.8 mmol) in DMF (50 ml) is added N,N-dimethyl-carbamothioyl chloride (6.94 g, 56.1 mmol). The mixture is stirred at RT for 14 h and at 60C for 3 h, poured onto water (100 ml) and extracted with EtOAc (3×50 ml). The combined organic layers are washed with water (2×50 ml), dried over sodium sulfate and concentrated. The residue is chromatographed (silica gel, 10% EtOAc/hexane) to give 4-(dimethyl-carbamothioyl)oxy-2-methyl-thiazole-5-carboxylic acid ethyl ester (5.7 g, 20.7 mmol, 55%). |
With sodium hydroxide; In N-methyl-acetamide; hexane; water; mineral oil; | A. A 5.05 g portion of 50% sodium hydride in mineral oil was washed with hexane and suspended in 100 ml of dimethylformamide. To this suspension, a solution of 19.57 g <strong>[20737-48-8]ethyl 4-hydroxy-2-methyl-5-thiazolecarboxylate</strong> in 100 ml of dimethylformamide was added dropwise resulting in the formation of a heavy yellow gel. The reaction mixture was diluted with 75 ml dimethylformamide and stirred for 30 minutes. A solution of 14.23 g of dimethylthiocarbamyl chloride in 50 ml dimethylformamide was added dropwise to the thick slurry, then the reaction mixture was heated at 85-95 for 45 minutes. The resulting brown suspension was cooled and poured into a cold solution of 5.7 g sodium hydroxide in 1200 ml water. The aqueous mixture was extracted once with benzene and twice with ether. The combined organic extracts were washed twice with water followed by brine, then dried over magnesium sulfate, filtered and the solvent evaporated giving an oil that partially crystallized. The crude reaction product was slurried in hexane, collected and dried giving 13.1 g of ethyl 4-[(dimethylamino)thioxomethyloxy]-2-methyl-5-thiazolecarboxylate, m.p. 87-90. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.16 g (53%) | In N,N-dimethyl-formamide; | Step A: Preparation of O-2-Carbomethoxy-4-fluorophenyl dimethylthiocarbamate To a solution of <strong>[391-92-4]methyl 5-fluorosalicylate</strong> (3.93 g, 23.1 mmol) in dry N,N-dimethylformamide (30 ml) was added sodium hydride (1.1 g, 50percent oil dispersion). After hydrogen gas evolution had ceased, the mixture was cooled in an ice-bath, and dimethylthiocarbamoyl chloride (3.71 g, 30.0 mmol) was added. The mixture was stirred at 80° C. for one hour, cooled, and poured into water (100 ml). The product was extracted with diethyl ether (2*), and the combined organic extracts were washed with water, 5percent aqueous potassium hydroxide, water, dried (sodium sulfate), and evaporated. The solid obtained was recrystallized from diethyl ether-hexane to afford 3.16 g (53percent) of O-2-carbomethoxy-4-fluorophenyl dimethylthiocarbamate. The 90 MHz NMR spectrum in chloroform-d was in accord with the desired structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In N-methyl-acetamide; mineral oil; | Example F 3,5-di-tert-butylthiophenol A solution of 103.2 g (0.5 mol) of 3,5-di-tert-butylphenol in 150 ml of dimethylformamide was added dropwise to a stirred suspension of 26.5 g (0.6 mol) of sodium hydride (approx. 60% suspension in mineral oil from which the oil had been removed with pentane) in 200 ml of dry dimethylformamide at room temperature. After evolution of hydrogen had ceased, 67.5 g (0.55 mol) of N,N-dimethylthiocarbamoyl chloride in 100 ml of dimethylformamide were added dropwise, and the reaction solution was stirred at 70 C. for 1 hour and then stirred into 500 ml of cold 5% strength potassium hydroxide solution, and the precipitate was filtered off, washed and dried. 84 g of this product were heated at 320 C. under nitrogen for 30 min. The solidified melt was recrystallized from diisopropyl ether to provide 42 g of a colorless solid (melting point 103-105 C.) which was dissolved in 200 ml of ether and added dropwise at room temperature to a suspension of 7 g (0.18 mol) of lithium aluminum hydride in 800 ml of ether. After the reaction was complete, 100 ml of 2N hydrochloric acid were added to the mixture, and the ether phase was separated off, washed with water, dried over magnesium sulfate and evaporated under reduced pressure. The residue provided 28.8 g of the title compound of melting point 47-49 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N-methyl-acetamide; | Step 1. Methyl 7-[dimethylaminothioxomethoxy)-naphthalene-2-carboxylate Sodium hydride (1.425 g) and <strong>[95901-05-6]methyl 7-hydroxynaphthalene-2-carboxylate</strong> (6.0 g) in dimethylformamide (200 ml) were stirred at 0 under nitrogen atmosphere for 1.5 hours. N,N-dimethylthiocarbamylchloride (11.0 g was added and the mixture was heated at 80 for 54 hours. The mixture was cooled, diluted with water (200 ml) and the resulting crystals were collected by filtration and dried to provide the title compound, m.p. 124.5-126. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With triethylamine; In tetrahydrofuran; hexane; dichloromethane; | A. 1-(3-Hydroxyphenyl)-2-(N-methyl-N-dimethylthiocarbamoyl)amino ethanol To a suspension of <strong>[61-76-7]phenylephrine hydrochloride</strong> (20.4 g, 0.1 mol) in tetrahydrofuran (500 ml) with triethylamine (27.8 ml) is slowly added dimethylthiocarbamoyl chloride (12.4 g, 0.1 mol). The reaction is stirred for 2 hours at room temperature. The mixture is filtered through celite and silica gel and the solvent is removed in vacuo giving an oil. The oil is purified by HPLC using hexane/methylene chloride gradient elution. Crystallization of the oil from fraction 6 gives 11.9 g (47% yield) of product, m.p. 95-79 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; potassium hydroxide; In N-methyl-acetamide; methanol; water; benzene; | To a solution of 112 grams (0.33 mole) of Bisphenol AF [2,2-bis(4-hydroxyphenyl)hexafluoropropane]in 700 milliliters of benzene was added 43.5 grams (0.66 mole) of 85% potassium hydroxide. The resulting solution was refluxed with a trap to remove water; benzene was then removed at reduced pressure. To the resulting salt was added 700 milliliters of dimethylformamide, the mixture was then cooled to 0 C., and then 100 grams (0.81 mole) of N,N-dimethylthiocarbamyl chloride was added. The resulting mixture was heated to room temperature, then to 60 C., and maintained at 60 C. for one hour. The product mixture was diluted with three liters of water and extracted twice with an 80:20 benzene/hexane solution. The organic phase was evaporated under reduced pressure to obtain a solid crystalline residue. The residue was recrystallized from a 5:1 methanol/ benezene solution to obtain 125 grams of a product melting at about 209-211 C. This product was the O-thiocarbamate ester of Bisphenol AF. Fifteen grams (0.3 mole) of the O-thiocarbamate ester of bisphenol AF was placed in a reaction vessel, and heated at 250 C. under argon for one hour. After cooling the product to room temperature, the glassy residue was recrystallized from 60 milliliters of methanol to obtain 11 grams of a product having a melting point of 141-144 C. This product was the S-thiocarbamate ester of the bisbenzenethiol derivative. Seventy-five grams (0.15 mole) of the above S-thiocarbamate ester was then placed in 400 milliliters of methanol, and a solution of 75 grams of potassium hydroxide in 200 milliliters of water was added. This mixture was refluxed for one hour, cooled and diluted with two liters of water. A solution of 165 milliliters of concentrated HCl in one liter of water was then added. A precipitate was obtained which was recrystallized from a 3:1 methanol-water mixture to obtain 50 grams of the product 2,2-bis(4-mercaptophenyl)hexafluoropropane (Compound 6). The dipotassium salt of Compound 6 was formed by reacting Compound 6 with a potassium-containing base. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16.7 g (24%) | In N,N-dimethyl-formamide; Petroleum ether; | Step B: Preparation of O-2-carbomethoxy-3-hydroxyphenyldimethylthiocarbamate A solution of <strong>[2150-45-0]methyl 2,6-dihydroxybenzoate</strong> (46 g, 0.27 mol) in N,N-dimethylformamide (100 ml) was added dropwise with stirring to a suspension of sodium hydride (50% dispersion in mineral) (14.4 g, 0.30 mol) in N,N-dimethylformamide (200 ml) cooled to 0 C. in an ice bath. After stirring for 1 hour at room temperature under a nitrogen atmosphere, a solution of dimethylthiocarbamoyl chloride (49.0 g, 0.40 mol) in N,N-dimethylformamide (100 ml) was added dropwise. Stirring was continued for 4 hours at room temperature followed by 1 hour at 80 C. The reaction mixture was cooled, poured into ice-water and extracted with diethyl ether. The combined extracts were washed with water (3*), saturated aqueous sodium chloride solution, dried (sodium sulfate), and evaporated. The residue was triturated with methanol followed by petroleum ether to give O-2-carbomethyoxy-3-hydroxyphenyl dimethylthiocarbamate as a white solid, yield (16.7 g (24%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | In methanol; potassium hydroxide; | EXAMPLE 5 Synthesis of methyl 2-[[(dimethylamino)carbonyl]thio]-3-pyridine carboxylate In a 100 mL flask was charged 3 g KOH pellets, 60 mL methanol and 7 g <strong>[10128-91-3]methyl 2-hydroxynicotinate</strong> and the mixture was stirred at room temperature for one half hour. Afterwards, 5.7 g of N,N-dimethylthiocarbamoyl chloride was added and the reaction mixture stirred for 4 hours. It was poured onto 100 mL ice water and filtered. The crystals were washed with water and dried to yield 5.3 g of methyl 2-[(dimethylamino)thioxomethoxy]-3-pyridine carboxylate (48%). NMR ((CH3)2SO-d6): delta 3.40 (s, 6H), 3.80 (s, 3H), 7.50 (t, 1H), 8.40(d, 1H), 8.60 (d, 1H), m.p. 125-127C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With 1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl-formamide; at 20℃; for 16h; | Preparation 8; 4-( 1,1-Dimethyl-propyl)-benzenethiol; 4-Cl.l -Dimethyl-propyl)- 1 -dimethylthiocarbamoyloxy-benzene; Stir a mixture of 4-( 1 , 1 - dimethyl-propyl)-phenol (1.96 g, 11.9 mmol), N,N-dimethylthiocarbamoyl chloride (2.94 g, 23.8 mmol) and DABCO (2.82 g, 25.1 mmol) in anhydrous DMF (30 mL) at room temperature for 16 h under a nitrogen atmosphere. Pour reaction onto ice and extract the mixture with EtOAc (3x75 mL). Combine the organic extracts and wash with 0.5 M aqueous HCl. Dry the organic phase over MgSO4 and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (4:1) to obtain the desired intermediate as a yellow solid (2.28 g, 76%). MS (ES+) m/z: 252.3 (M+Eta)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With triethylamine; In 1,4-dioxane; for 3h; | A mixture of <strong>[405-05-0]3-fluoro-4-hydroxy benzaldehyde</strong> (5.00 g), N,N-dimethyl thiocarbamoyl chloride (5.29 g), triethylamine (4.33 g), N,N-dimethyl amino pyridine (436 mg) and dioxane (50 ml) was stirred for 3 hours. After addition of water, the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was washed with isopropyl ether to give a title compound (7.05 g) as blackish brown crystal. The yield was 71 percent. 1H-NMR(CDCl3): 3.39(3H, s), 3.47(3H, s), 7.27-7.35(1H, m), 7.67-7.74(2H, m), 9.97(1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In tetrahydrofuran; water; | Synthesis of 1-(4-Chloro-3-methylsulfanyl-phenyl)-piperazine To <strong>[183802-98-4]5-Bromo-2-chlorophenol</strong> (1.7 g, 0.0087 mol) in 9 mL of water was added potassium carbonate (0.5 g, 0.0087 mol), and the mixture was stirred for 15 min, then cooled to 10 C. N,N-dimethylthiocarbamylchloride (1.4 g, 0.0117 mol) in 3 mL of THF was added, the reaction was allowed to warm to ambient temperature, and was stirred for 2 hours. The mixture was extracted with eihyl acetate, washed once each with water and brine, and concentrated to give O-(5-bromo-2-chlorophenyl) dimethylthiocarbamate as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; triethylamine; In 1,4-dioxane; for 30h;Heating / reflux; | Example 25: (E) -4- (3, 5-dimethoxystyryl) benzenethiol ARS27.; A solution of <strong>[537-42-8]pterostilbene</strong> (lOOmg, 0.39mM) dimethyl thiocarbonyl chloride (58mg, 0.47mM) trietylamine (109muL,0.78mM) dimethylamino pyridine (4.7mg, 0.039mM) in dioxane(1OmL) was refluxed for 3Oh. The mixture was poured into water and extracted with ethyl acetate. The solvent was evaporated, the crude mixture was purified by column chromatography eluting with hexanes: ethyl acetate (7:3) and afforded (E) -0-4- (3, 5-dimethoxystyryl) phenyl dimethylcarb- amothioate . |
Yield | Reaction Conditions | Operation in experiment |
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100% | Example BOA DIMETHYL-THIOCARBAMIC ACID 0- (4-BROMO-2, 3-dichloro- phenyl) ester To a stirred suspension of NaH (95%, 1.45 g, 57.5 mmol) in DMF (100 mL) was added dropwise a solution of <strong>[1940-44-9]4-bromo-2,3-dichloro-phenol</strong> (prepared from 2,3-dichlorophenol according to WO 00/59880, 12.1 g, 50.0 mmol) in DMF (25 mL) at 0C. After stirring at the same temperature for 30 min, a solution of dimethylthiocarbonyl chloride (7.11 g, 57.5 mmol) in DMF (25 mL) was added dropwise. The reaction mixture was stirred at room temperature overnight. The mixture was diluted with water (500 ML) and extracted with ether. The combined organic layers were washed with brine, dried, and concen- trated to give the title compound (16.6 g, 100%) as a white solid, which was used in the next step without further purification. 1H NMR (CDC13, 400 MHz) 5 7.58 (d, J=9.0 Hz, 1H), 7.00 (d, J=9.0 Hz, 1H), 3.47 (s, 3H), 3.39 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
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<strong>[79370-78-8]3,5-Dicyanohydroxybenzene</strong> (W002/085860) (50g, 350 mmol) in 1-methyl-2- pyrrolidinone (200mL) was added to a stirred suspension of sodium carbonate (48g, 450mmol) in 1-methyl-2-pyrrolidinone (200nnL) at 0C under a nitrogen atmosphere. After warming to rt, the resulting mixture was stirred at ambient temperature for 30 min. Then a solution of dimethylthiocarbamoyl chloride (56g, 450mmol) in 1-methyl-2-pyrrolidinone (200mL) was added. The reaction mixture was stirred at rt for 30 min, then at 70C for 16h - After this time, the reaction mixture was cooled to rt and water (200mL) was added. The resultant white precipitate was collected by filtration and dried in a vacuum oven at 55C for 48 hours to give the title compound as a colourless solid (53g). |
Yield | Reaction Conditions | Operation in experiment |
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Example 22N-{4-[7-tert-Butyl-5-(2-oxo-1,2-dihydro-pyridin-3-yl)-benzo[b]thiophene-3-carbonyl]-morpholin-2-ylmethyl}-methanesulfonamide (112) step 1 -The neat thiocarbamate 102a (9.2 g, prepared by acylation of 2-tert-butyl-4-bromo-phenol with N,N-dimethyl thiocarbamoyl chloride) was heated with a heat gun for 20 min. (At 20 min extraneous peaks began to be detectable by TLC). The reactant was cooled and purified by SiO2 chromatography (Analogix, 80 g) eluting with an EtOAc/hexane gradient to afford 4.6 g (50%) of 102b as a light brown solid. |
Yield | Reaction Conditions | Operation in experiment |
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With 1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl-formamide; at 20℃; | EXAMPLE 52; [(5-Fluoro-4-hydroxy-2-oxo-2H-thiochromene-3-carbonyl)-amino]-acetic acid a) Dimethyl-thiocarbamic acid 0-(2-acetyl-3-fluoro-phenyl) ester[0313] l-(2-Fluoro-6-hydroxy-phenyl)-ethanone (2.5g, 16.22 mmol) (available from Apollo Scientific) was dissolved in anhydrous DMF (20 inL.) Dimethylthiocarbamoyl chloride (2.2 g, 17.84 mmol) and DABCO (2.Og, 17.84 mmol) were added sequentially in one portion. The reaction was permitted to stir overnight at ambient temperature. The reaction was quenched by pouring it into a mixture of IN HCl-ice. The oily residue was extracted with dichloromethane and dried over sodium sulfate. The crude residue was purified by SGC (20% ethyl acetate in hexanes) to provide the title compound (2.93 g.) 1H NMR (200 MHz, CDCl3): delta (ppm) = 7.407 (dd, IH), 7.026 (t, IH), 6.876 (d, IH), 3.404 (s, 3H), 3.341 (sd, 3H), 2.58 (d, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl-formamide; at 20℃; for 20h; | b) 4-Chloro-2-dimethylthiocarbamoyloxy-benzoic acid methyl ester [0331] To a mixture of the above ester (6.48 g, 34.7 mmol) in DMF (40 mL) was added DABCO (11.6 g, 104 mmol) and dimethylthiocarbamoyl chloride (4.5 g, 36.5 mmol). The resultant mixture was stirred at rt for 20 h and poured into EtOAc / I N HCl aq solution. Organic phase was washed with 1 N HCl solution, saturated NaHCO3 solution and brine. It was filtered, dried over Na2SO4, filtered and concentrated to provide the title compound (8.86 g) as pale yellow solid. 1H NMR (200 MHz, CDCl3): delta (ppm) = 7.93 (d, J = 8.2 Hz, 1 H), 7.28 (dd, J = 8.5, 2.2 Hz, 1 H), 7.13 (d, J = 2.0 Hz, 1 H). 3.83 (s, 3 H), 3.46 (s, 3 H), 3.38 (s, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 - 20℃; for 2h; | Preparative Example 5PREPARATION OF O-(2-CHLORO-4-METHOXYPHENYL) DIMETHYLTHIOCARBAMATETo a solution of the <strong>[18113-03-6]2-chloro-4-methoxyphenol</strong> (25.4 g, 160.2 mmol), in anhydrous THF (254 mL) was added DBU (24.8 mL, 176.1 mmol) and N,N-dimethylthiocarbamoyl chloride (20.8 g, 168.2 mmol). The mixture was stirred initially at 0 C. and then warmed to room temperature and stirred for an additional 2 hrs. The mixture was diluted with EtOAc and washed with cold 2N HCl, water, 5% aq. NaHCO3 solution and brine. The separated organic phase was dried with Na2SO4, filtered and evaporated to dryness. The resulting residue was purified by silica gel chromatography (230-400 mesh) with 20% EtOAc-hexanes as the eluent to give of O-(2-chloro-4-methoxyphenyl) dimethylthiocarbamate.1H NMR (400 MHz, CDCl3) delta (ppm): 7.03 (d, J=8.9 Hz, 1H), 6.95 (d, J=2.0 Hz, 1H), 6.80 (dd, J=9.0 Hz, 2.9 Hz, 1H), 3.78 (s, 3H), 3.45 (s, 3H), 3.36 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In acetone; for 48h;Reflux; | N,N-Dimethylthiocarbamoyl chloride (0.45 mmol) and Cs2CO3 (0.45 mmol) were added to a solution of dinaphthylmethane 1 or 2 (0.3 mmol) in acetone (6 mL). The reaction mixture was refluxed for 48 h with stirring. Acetone was distilled off, and 1 HCl (10 mL) was added to the residue. The resulting precipitate was filtered and washed with H2O (50 mL). The product was dried for 3 h at 65-70 /1 mm Hg. 2,2'-Di(thiocarbamoyl)dinaphthylmethane (9) (Table 2). Light-yellow powder. 1 NMR (400 MHz, CDCl3), delta: 2.07 (s, 6, NCH3), 3.08 (s, 6, NCH3), 4.81 (s, 2, 2), 7.04 (d, 2, J = 8.7 Hz, -3), 7.48 (dd, 2, J = 6.8 Hz, J = 8.2 Hz, -7), 7.51 (dd, 2, J = 6.8 Hz, J = 8.2 Hz, -6), 7.74 (d, 2, J = 9.2 Hz, -4), 7.85 (d, 2, J = 7.8 Hz, -8), 8.33 (d, 2, J = 8.3 Hz, -5). 13 NMR (100.5 MHz, CDCl3), delta: 24.03 (CH2), 37.28 (N-CH3), 42.72 (N-CH3), 123.09 (C-3), 124.60 (C-5), 125.32(-7), 126.14 (C-6), 127.52 (C-4), 128.83 (C-8, C-1), 132.36 (C-10), 133.16 (C-9), 149.81 (C-2), 186.15 (CS). IR (Nujol): 2953, 2924, 2854, 1538, 1463, 1379, 1281, 1217, 1121, 820, 746 cm-1. Anal. Calcd for C27H26N2O2S2: , 68.32; , 5.52; N, 5.90. Found: , 68.61; , 5.48; N, 5.68. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
132.2 2-Chloro-5-dimethylthiocarbamoyloxy-benzoic acid methyl esterTo a solution of intermediate 132.1 (10 g) in 1-methyl-2-pyrrolidinone (8 ml.) was added 1 ,4-diazabicyclo[2.2.2]octane (7.51 g) and the reaction mixture was heated to 50C. A solution of dimethylthiocarbamoyl chloride (6.96 g) in 1-methyl-2-pyrrolidinone (2 ml.) was added dropwise and the reaction mixture was stirred for 3h at 50C. It was quenched with H20 (85 ml.) over 10 min, heated to 50C and cooled to RT. It was extracted with EtOAc, the organic phase was dried over MgS04 and concentrated in vacuo. A light yellow solid precipitated out the oily residue and was filtered to give 10 g of the crude titled compound. LC-MS (B): tR = 0.79 min; [M+H]+: 273.90 | ||
With 1,4-diaza-bicyclo[2.2.2]octane; In 1-methyl-pyrrolidin-2-one; at 50℃; for 3h; | 132.2 2-Chloro-5-dimethylthiocarbamoyloxy-benzoic acid methyl ester To a solution of intermediate 132.1 (10 g) in 1-methyl-2-pyrrolidinone (8 mL) was added 1,4-diazabicyclo[2.2.2]octane (7.51 g) and the reaction mixture was heated to 50 C. A solution of dimethylthiocarbamoyl chloride (6.96 g) in 1-methyl-2-pyrrolidinone (2 mL) was added dropwise and the reaction mixture was stirred for 3 h at 50 C. It was quenched with H2O (85 mL) over 10 min, heated to 50 C. and cooled to RT. It was extracted with EtOAc, the organic phase was dried over MgSO4 and concentrated in vacuo. A light yellow solid precipitated out the oily residue and was filtered to give 10 g of the crude titled compound. LC-MS (B): tR=0.79 min; [M+H]+: 273.90 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61.8% | To a solution of <strong>[112204-58-7]5-bromo-2-fluoro-phenol</strong> (1000 mg, 5.24 mmol) in DMF (10 mL) were added NaH (180.55 mg, 7.85 mmol). After 10 mins, N,N- dimethylcarbamothioyl chloride (970.73 mg, 7.85 mmol) was added. The reaction mixture was stirred at room temperature for 20h. Water (30 mL) and DCM (30 mL) were added. The organic layer was washed with brine, dried (Na2S04) and evaporated to dryness. The crude products were purified by flash column chromatography to obtain 0-(5-bromo-2-fluoro-phenyl) N,N-dimethylcarbamothioate (900 mg, 61.80%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | General procedure: An equivalent of appropriate salicylanilide (1 mmol) was suspendedunder vigorous stirring in dry dichloromethane (DCM;10 mL), and then triethylamine (1.5 of equivalents) was added inone portion. The mixture was stirred for 5 min to allow completedissolution of the salicylanilide due to formation of its triethylammoniumsalt. Then, appropriate (thio)carbamoyl chloride (1.5 ofequivalents) was added in one portion, and the mixture was stirredat room temperature for 48 h (carbamates) or 72 h (thiocarbamates).The reaction was monitored using TLC. Then, the solutionwas evaporated till dryness, ethyl acetate was added and the suspensionwas stored at 4 C for approximately 30 min. Then, theprecipitate was removed by filtration, the filtrate was collected,partly evaporated and then n-hexane was added to initiate crystallisation.After 24 h at 4 C, the precipitate was filtered to giveresulting (thio)carbamates 1-5. Products were recrystallised fromethyl acetate, if necessary.When dry acetonitrile (MeCN) was used as the solvent at rt, thereaction time was shortened to 18 h for carbamates and 24 h forthiocarbamates. Under refluxing in acetonitrile, the reaction timeof 2.5 h was sufficient for carbamates and 5 h for thiocarbamates.However, these methods produced similar yields and purity ofthe product as the described general method performed in dichloromethaneat rt. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | S-pyrimidin-5- l N,N-dimethylcarbamothioate 15 (used during synthesis of 20) (I5) (a) Dimethyl-thiocarbamic acid pyrimidin-5-yl ester NaH (60% dispersion, 450 mg, 11.25 mmol) was added to <strong>[26456-59-7]5-hydroxypyrimidine</strong> (1.03 g, 10.72 mmol) in dry DMF (10 mL) at rt. The reaction mixture was stirred for 10 min, then Nu,Nu-dimethylthiocarbamoyl chloride (1.39 g, 11.25 mmol) was added. The reaction mixture was heated to 90 C for 1 h, then stirred at rt for 18 h. The reaction mixture was poured into brine (40 mL) and was extracted with DCM (3 x 30 mL). The combined organic extracts were passed through a phase separator cartridge and the solvent removed in vacuo to give the crude product which was purified by flash column chromatography (Biotage Isolera 4) eluting with neat iso-hexane to 50% EtOAc / iso- hexane to give the title compound as a yellow solid (212 mg, 1.16 mmol, 1 1 %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.7% | To a solution of <strong>[74115-12-1]5-chloropyridin-3-ol</strong> (3.0 g, 23.2 mmol) in N,N-dimethylformamide (40 mL) was added NaH (1.5 g, 40% in mineral, 25.5 mmol) at 0C, then the mixture was stirred at 0C for 30 min. Dimethylthiocarbamoyl chloride (3.15 g, 25.5 mmol) was added to the mixture, then it was stirrred at room temperature for 20 h. The reaction was followed by TLC. The reaction was quenched with water (150 mL). The mixture was extracted with CH2CI2 (80 mL X 3) and the aqueous phase was discarded. The combined organic layers were washed with brine (80 mL X 2), dried over Na2S04, filtered and concentrated in vacuo to afford crude product, which was purified by Biotage (EA:PE=1 :5 to 1 :2, ISCO 40 g, 40 mL/min, normal phase silica, uv254). 4 g (79.7 %>) of the title compound as brown oil was obtained. ESI-MS m/z calcd for [C8H9C1N20S]+ [M+H]+: 217.0; found: 217.0. | |
28.7% | To a solution of <strong>[74115-12-1]5-chloropyridin-3-ol</strong> (10 g, 0.10 mol) in N,N-dimethylformamide (200mL) was added NaH (1.90 g, 0.10 mol) at 0C. The reaction mixture was stirred at 0C 30 minutes followed by addition of Dimethylthiocarbamoyl chloride (10.50 g, 0. 10 mol) followed by stirring at room temperature 20h. The reaction was quenched with water (500 mL) and extracted with dichloromethane (500 mL X 3). The combined organics were washed with brine (400 mL X 3), dried over Na2S04, filtered and the solvents where removed in vacuo. The crude product was purified by chromatography on a combiflash (EtOAc: PE=1 :5) to give 0-[(5-chloro-3-pyridyl)] N,N-dimethylcarbamothioate 6.2 g (28.7 %) as brown oil. m/z calcd for [C8H9C1N20S]+ [M+H]+: 217.0; found: 217.0 | |
28.7% | To a solution of <strong>[74115-12-1]5-chloropyridin-3-ol</strong> (10 g, 0.10 mol) in N,N-dimethylformamide(200mL) was added NaH (1.90 g, 0.10 mol) at 0C. The reaction mixture was stirred at0C 30 minutes followed by addition of Dimethylthiocarbamoyl chloride (10.50 g, 0. 10 mol) followed by stirring at room temperature 20h. The reaction was quenched with water (500 mL) and extracted with dichloromethane (500 mL X 3). The combined organics were washed with brine (400 mL X 3), dried over Na2SO4, filtered and the solvents where removed in vacuo. The crude product was purified by chromatography on a combiflash (EtOAc: PE=1 :5) to give the title compound 6.2 g (28.7 %) as brown oil.m/z calcd for [C8H9ClN2OS] [M+H]: 217.0; found: 217.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With 1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl-formamide; at 20℃; | A mixture of 4-bromo-7-hydroxy-2, 3 -dihydro- lH-inden-1 -one (900 mg, 4.0 mmol) dissolved in DMF (15 mL) was treated with DABCO 33LV (1.3 mL, 12 mmol) and Nu,Nu-dimethylcarbamothioyl chloride (1.5 g, 12 mmoil) was stirred overnight at ambient temperature. The reaction was treated with water and ethyl acetate and separated. The aqueous layer was extracted with ethyl acetate then the combined organic layers were washed with water and saturated NaCl. After drying, the organic layer was concentrated in vacuo and purified by chromatography on Si02 eluting with a gradient of ethyl acetate / hexanes, (670 mg, 54%). 1H MR (400 MHz, CDC13): delta 7.78-7.76 (d, 1H), 6.97-6.95 (d, 1H), 3.44 (s, 3H), 3.41 (s, 3H), 3.08 (m, 2H), 2.76-2.69 (m, 2H). |
54% | With 1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl-formamide; at 20℃; | : A mixture of 4-bromo-7-hydroxy-2, 3 -dihydro- liT-inden-l -one (900 mg, 4.0 mmol) dissolved in DMF (15 mL) was treated with DABCO 33LV (1.3 mL, 12 mmol) and N,N-dimethylcarbamothioyl chloride (1.5 g, 12 mmoil) was stirred overnight at ambient temperature. The reaction was treated with water and ethyl acetate and separated. The aqueous layer was extracted with ethyl acetate then the combined organic layers were washed with water and saturated NaCl. After drying, the organic layer was concentrated in vacuo and purified by chromatography on Si02 eluting with a gradient of ethyl acetate / hexane, (670 mg, 54%). 1H NMR (400 MHz, CDCI3): d 7.78-7.76 (d, 1H), 6.97-6.95 (d, 1H), 3.44 (s, 3H), 3.41 (s, 3H), 3.08 (m, 2H), 2.76-2.69 (m, 2H). |
670 mg | With 1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl-formamide; at 20℃; | 1005911 Step C: Preparation of O-(7-bromo-3-oxo-2.3-dihydro-1H-inden-4-yl) dimethylcarbamothioate: A mixture of 4-bromo-7-hydroxy-2, 3 -dihydro- 1H-inden- 1-one (900 mg, 4.0 mmol) dissolved in DMF (15 mL) was treated with DABCO 33LV (1.3 mL, 12 mmol) and N,N-dimethylcarbamothioyl chloride (1.5 g, 12 mmoil) was stirred overnight at ambient temperature. The reaction was treated with water and ethyl acetate and separated. The aqueous layer was extracted with ethyl acetate then the combined organic layers were washed with water and saturated NaC1. After drying, the organic layer was concentrated in vacuo and purified by chromatography on 5i02 eluting with a gradient of ethyl acetate / hexanes, (670 mg, 54%). ?H NIVIR (400 IVIFIz, CDC13): 7.78-7.76 (d, 1H), 6.97-6.95 (d, 1H), 3.44 (s, 3H), 3.41 (s, 3H), 3.08 (m, 2H), 2.76-2.69 (m, 2H). |
670 mg | With 1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl-formamide; at 20℃; | A mixture of 4-bromo-7-hydroxy-2,3-dihydro-lH-inden-l-one (900 mg, 4.0 mmol) dissolved in DMF (15 mL) was treated with DABCO 33LV (1.3 mL, 12 mmol) and Nu,Nu-dimethylcarbamothioyl chloride (1.5 g, 12 mmoil) was stirred overnight at ambient temperature. The reaction was treated with water and ethyl acetate and separated. The aqueous layer was extracted with ethyl acetate then the combined organic layers were washed with water and saturated NaCl. After drying, the organic layer was concentrated in vacuo and purified by chromatography on Si02 eluting with a gradient of ethyl acetate / hexane, (670 mg, 54%). 1H NMR (400 MHz, CDCl3): delta 7.78-7.76 (d, 1H), 6.97-6.95 (d, 1H), 3.44 (s, 3H), 3.41 (s, 3H), 3.08 (m, 2H), 2.76-2.69 (m, 2H). |
670 mg | With 1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl-formamide; at 20℃;Large scale; | a mixture of <strong>[81945-13-3]4-bromo-7-hydroxy-2,3-dihydro-1H-inden-1-one</strong> (900 mg, 4.0 mmol) dissolved in DMF (15 mL) was treated with DABCO 33LV (1.3 mL, 12 mmol) and N,N-dimethylcarbamothioyl chloride (1.5 g, 12 mmol) was stirred overnight at ambient temperature. The reaction was treated with water and ethyl acetate and separated. The aqueous layer was extracted with ethyl acetate then the combined organic layers were washed with water and saturated NaCl. After drying, the organic layer was concentrated in vacuo and purified by chromatography on SiO2 eluting with a gradient of ethyl acetate/hexanes, (670 mg, 54%). 1H NMR (400 MHz, CDCl3): delta 7.78-7.76 (d, 1H), 6.97-6.95 (d, 1H), 3.44 (s, 3H), 3.41 (s, 3H), 3.08 (m, 2H), 2.76-2.69 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With potassium tert-butylate; copper(I) bromide; In tetrahydrofuran; at 60℃; for 4h;Schlenk technique; | General procedure: A mixture of 2-iodoanilines (1.0 mmol), THF (3 mL), and t-BuOK (3 mmol) was stirred in a 10-mL sealed Schlenk tube for 5 min, and then dimethylthiocarbamoyl chloride (1.2 mmol) and CuBr (10 mol %) were added. The reaction mixture was heated at 60 C until completion as indicated by TLC. Then the mixture was cooled down to room temperature and quenched with sat. NH4Cl solution (5 mL). The aqueous phase was extracted with EtOAc (3 x10 mL). The combined organic phases were dried (Na2SO4), and the solvent was removed under reduced pressure. The obtained crude product was purified by flash column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With potassium carbonate; copper dichloride; In tetrahydrofuran; at 60℃; for 2.5h; | General procedure: To a dried tube equipped with a magnetic stirrer and a septum, 2-aminophenol (1.0 mmol) was dissolved in THF (2.5 mL), and K2CO3 (1.0 mmol) was added. The mixture was stirred for 5 minutes, thiocarbamoyl chloride (3.0 mmol) and copper chloride (5 mol percent) were added. The reaction mixture was then heated at 60 °C and checked by TLC until the starting material was finished. The reaction was cooled down to room temperature, quenched with sat. NH4Cl solution (5 mL) and extracted with ethyl acetate, dried over anhydrous Na2SO4 and then evaporated under vacuum. The residue was purified by flash column chromatography to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium tert-butylate; bis(dibenzylideneacetone)-palladium(0); In tetrahydrofuran; at 60℃; | General procedure: A dried tube, equipped with a magnetic stirred and a septum, 2-chloroanilines (1.0 mmol) was dissolved in DMSO(3 mL), and t-BuOK (3 mmol) was added. The mixture was stirred for 5 minutes, and thendimethylthiocarbamoyl chloride (1.2 mmol) and bis(dibenzylideneacetone) palladium (5 mol%) were added.the reaction mixture was then heated at 100 C and checked by TLC until the starting material was finished. Thereaction was cooled down to room temperature, and then quenched with sat. NH4Cl solution (5 mL) and extractedwith ethyl acetate, dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flashcolumn chromatography to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With potassium tert-butylate; bis(dibenzylideneacetone)-palladium(0); In tetrahydrofuran; at 60℃; | General procedure: A dried tube, equipped with a magnetic stirred and a septum, 2-chloroanilines (1.0 mmol) was dissolved in DMSO(3 mL), and t-BuOK (3 mmol) was added. The mixture was stirred for 5 minutes, and thendimethylthiocarbamoyl chloride (1.2 mmol) and bis(dibenzylideneacetone) palladium (5 mol%) were added.the reaction mixture was then heated at 100 C and checked by TLC until the starting material was finished. Thereaction was cooled down to room temperature, and then quenched with sat. NH4Cl solution (5 mL) and extractedwith ethyl acetate, dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flashcolumn chromatography to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With potassium tert-butylate; bis(dibenzylideneacetone)-palladium(0); In tetrahydrofuran; at 60℃; | General procedure: A dried tube, equipped with a magnetic stirred and a septum, 2-chloroanilines (1.0 mmol) was dissolved in DMSO(3 mL), and t-BuOK (3 mmol) was added. The mixture was stirred for 5 minutes, and thendimethylthiocarbamoyl chloride (1.2 mmol) and bis(dibenzylideneacetone) palladium (5 mol%) were added.the reaction mixture was then heated at 100 C and checked by TLC until the starting material was finished. Thereaction was cooled down to room temperature, and then quenched with sat. NH4Cl solution (5 mL) and extractedwith ethyl acetate, dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flashcolumn chromatography to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.2% | With triethylamine; In dichloromethane; at 20℃;Cooling with ice; | 0.05 mol (8.91 g) of 4- (1-piperazinyl) phenol was dissolved in 100 mL of methylene chloride, 0.05 mol (5.05 g) of triethylamine was added, Ice-salt bath under stirring for 10 minutes, 0.05 mol (6.18 g) of dimethylaminothioformyl chloride was slowly added, Remove the ice bath after 1 hour, Stir overnight at room temperature. The reaction solution was washed with water, Washed with saturated salt three times, Dried over anhydrous magnesium sulfate, After filtration, it was evaporated to dryness to give 10.12 g of 4-piperazinophenol dimethylaminothiocarbamate in a yield of 81.2%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With 1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl acetamide; at 0 - 20℃; for 48h;Inert atmosphere; | To a solution of 1-3 2,5-dihydroxyterephthalaldehyde (423 mg, 2.546 mmol, 1 eq) andDABCO (1.142 g, 10.184 mol, 4 eq) in dry DMA (11.3 mL) was added at 000 dimethylthiocarbamoyl chloride (1.252 g, 10.184 mmol, 4 eq) in 3.7 mL of dryDMA). The mixture was stirred at room temperature for 48 h under inert atmosphere. The white precipitate was filtrated and washed with water. Drying of the resulting solid gave a white powder (618 mg, 71 %).White solid; mp: 226.1 - 228.6 00; HRMS (ESI) [M + H] found 341.0623, calculated341.0624 for [O14H17N204S2] 1H NMR (300 MHz, 0D013) 6 ppm = 10.07 (s, 2 H, OHO),7.67 (s, 2 H, Ar), 3.52 - 3.48 (m, 6 H, OH3), 3.45 (s, 6 H, OH3); 1H NMR (400 MHz, DMSO)6 ppm = 10.03 (s, 2 H, OHO), 7.65 (s, 2 H, Ar), 3.43 (s, 6 H, OH3), 3.41 (s, 6 H, OH3) ; 130NMR (400 MHz, DMSO) 6 ppm = 187.3 (CHO), 185.5 (CS), 151.8 (CArS), 133.1 (CAr CHO), 123.9 (CArH), 42.9 (OH3), 38.5 (OH3) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.0% | To a solution of <strong>[13659-24-0]3-bromo-4-chlorophenol</strong> (2 g, 9.64 mmol) in N,N-dimethylformamide (30 mL) was added NaH (244 mg, 10.6 mmol) at 0 C, then the mixture was held at same temperature with stirring on for 30 min. dimethylthiocarbamoyl chloride (1.311 g, 10.6 mmol) was added to the mixture, then it was stirred at room temperature for 20 h. The reaction was quenched with water (50 mL). The mixture was extracted with CH2C12 (50 mL X 3) and the aqueous phase was discarded. The combined organic layers were washed with brine (40 mL X 3), dried over Na2S04, filtered and concentrated in vacuo to afford crude product, which was purified by flash chromatography using a Biotage (EA:PE=0~20%, ISCO 40 g, 40 mL/min, normal phase silica, uv254). 2.5 g (88.0 %) of the title compound as brown was obtained. NMR (400 MHz, CDC13) delta 7.45 (d, J= 8.7 Hz, 1H), 7.36 (d, J= 2.7 Hz, 1H), 7.00 (dd, J= 8.7, 2.7 Hz, 1H), 3.44 (s, 3H), 3.33 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54.6% | With 1,4-diazabicyclooctane; In tetrahydrofuran; at 20℃; for 16h; | A solution of <strong>[40673-25-4]4-chloropyridin-2-ol</strong> (1 g, 10 mmo 1) and 1 ,4-diazabicyclooctane (1 .8 g,16.02 mmol) in tetrahydrofuran (30 ml) was added N,N-dimethylcarbamothioyl chloride (1.3 g, 10.68 mmol). The reaction mixture was stirred at r.t over 16 h The reaction mixture was evaporated to dryness and the residue was purified by flash chromatography (PE : EA =10% - 50% ) to give the title compound 800 mg (54.6%). m/z calcd for [C8H9ClN2OS] [M+H]: 217.0; found: 217.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With pyridine; copper(l) iodide; sodium hydroxide; at 60℃; for 0.166667h;Microwave irradiation; Green chemistry; | Add 1 mmol of o-phenylenediamine to the reaction vessel.Add 0.05 mmol of cuprous iodide sequentially.1 mmol of sodium hydroxide, N,N-dimethylaminothioformyl chloride 2.5 mmol,3 ml pyridine.Heated to 60 C at 120 W in a microwave reactorContinuous reaction for 10 min.After the reaction is completed, it is cooled to room temperature.Concentrated under reduced pressure,The product is purified by column chromatography.A white solid was obtained in 88% yield. |
87% | With iron(III) chloride; caesium carbonate; In tetrahydrofuran; at 60℃; for 5.0h;Green chemistry; | Add 1 mmol of o-phenylenediamine to the reaction vessel.Add 0.1 mmol of ferric chloride in sequence,Cesium carbonate 1 mmol,N,N-dimethylaminothioformyl chloride 2.5 mmol,3 ml of tetrahydrofuran. Heat to 60 C for 5 h. After the reaction is completed, it is cooled to room temperature.Concentrated under reduced pressure, the product was purified by column chromatography.A white solid was obtained in a yield of 87%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere; | Under a nitrogen atmosphere, the compound 1 (190 mg, 0.79 mmol) and N-diisopropylethyl-amine (0.5 mL) was dissolved by dry CH2Cl2 (16 mL) and stirred at 0 C. Then, the solution of dimethyl-thiocarbamoyl chloride (495 mg, 4.0 mmol) in dry CH2Cl2 (3 mL) was added dropwise. After being stirred for 90 min, the resulting mixtures were stirred overnight at room temperature. After that, the mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate, 10:1, v/v) toyield probe BS1 as white solids (161 mg, 62%). 1H NMR (400 MHz, CDCl3) delta 2.49 (s, 3H), 3.53 (s, 3H), 3.54 (s,3H), 7.10 (d, J = 8.4 Hz, 1H), 7.34 (dd, J = 8.4 Hz &J = 1.2 Hz, 1H), 7.41 (td, J = 7.6 Hz and J = 1.2 Hz, 1H),7.52 (td, J = 8.0 Hz & J = 1.2 Hz, 1H), 7.92 (dd,J = 8.0 Hz & J = 0.4 Hz, 1H), 8.09 (d, J = 8.0 Hz, 1H),8.18 (d, J = 1.6 Hz, 1H). 13C NMR (100 MHz, d6-DMSO)delta 20.94, 39.20, 43.53, 121.35, 123.22, 124.58, 125.13,126.15, 126.52, 130.19, 131.94, 135.63, 136.28, 149.50,152.84, 162.71, 187.04. ESI-MS m/z: 328.8 [M + H] +. |
62% | With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;Cooling with ice; | To a 100 ml round bottom flask was added anhydrous dichloromethane (16 mL),Compound 1 (190 mg, 0.79 mmol) and N, N-diisopropylethylamine (0.5 mL) were stirred well.Then a solution of N, N-dimethylaminothioformyl chloride (395 mg, 4.0 mmol) in dichloromethane (3 mL) was added dropwise,After 90 minutes of reaction in an ice water bath,Transfer to room temperature and react overnight.After the reaction was completed, silica gel was added, and the solvent was removed by using a rotary evaporator.Silica gel column separation and purification (petroleum ether: ethyl acetate = 10: 1, v / v),The obtained white solid (161 mg, 62%) was a fluorescent probe molecule BS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene; for 5h;Reflux; | General procedure: Taking the synthesis of 18 3-(trifluoromethyl)phenyl 1-isothiocyanate as an example, 19 3-(trifluoromethyl)aniline (2.38g, 14.77mmol, 1 eqv) and 20 dimethylamino thiocarbonyl chloride (1.92g, 15.50mmol, 1.05 eqv) were added in dry 21 toluene (20mL) at room temperature, and then the reaction mixture was refluxed for 5h. After the reaction mixture was cooled down to room temperature, the solid dimethylamine hydrochloride was filtered off, and the collected toluene fraction was removed under reduced pressure. Colorless oil (2.55g, 85%) was obtained and used in the next step without additional purification. The other aromatic isothiocyanates were synthesized in the same way. |
Tags: 16420-13-6 synthesis path| 16420-13-6 SDS| 16420-13-6 COA| 16420-13-6 purity| 16420-13-6 application| 16420-13-6 NMR| 16420-13-6 COA| 16420-13-6 structure
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