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CAS No. : | 614-23-3 | MDL No. : | MFCD00041191 |
Formula : | C8H8N2OS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DQMWMUMCNOJLSI-UHFFFAOYSA-N |
M.W : | 180.23 | Pubchem ID : | 2735473 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 49.94 |
TPSA : | 87.21 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) : | -6.36 cm/s |
Log Po/w (iLOGP) : | 1.36 |
Log Po/w (XLOGP3) : | 1.47 |
Log Po/w (WLOGP) : | 0.66 |
Log Po/w (MLOGP) : | 0.97 |
Log Po/w (SILICOS-IT) : | 1.52 |
Consensus Log Po/w : | 1.2 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.06 |
Solubility : | 1.59 mg/ml ; 0.0088 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.91 |
Solubility : | 0.223 mg/ml ; 0.00124 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.19 |
Solubility : | 1.16 mg/ml ; 0.00646 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.15 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P501-P270-P264-P301+P310+P330-P405 | UN#: | 2811 |
Hazard Statements: | H301 | Packing Group: | Ⅲ |
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 |
---|---|---|
With methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With copper(l) iodide; sodium hydroxide In dimethyl sulfoxide at 90℃; for 2.5h; | |
With sodium azide; lead(II) oxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(hydrolysis); | ||
beim Erhitzen; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 130 - 150℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 120℃; | ||
at 120℃; | ||
In acetone |
In toluene at 100℃; | 2.10. General Procedure for the Preparation of Compoundsb General procedure: A selected arylcarboxylic acid (10 mmol) was solved inSOCl2 (50 mL), which was heated to 90 °C and stirred for 1-2 h until the reaction was completed. The crude product (a1-a30) was furnished after the removal of SOCl2 under reducedpressure [64-65]. To the resulting residue, 50 mL of toluenewas added and stirred for 30 min at room temperature. Thiourea(40 mmol) was subsequently added, and the reactionsolution was heated to 100 °C for 1.5-2 h [66, 67]. At the endof the reaction (monitored by TLC), the solvent was removedunder vacuum, and excess saturated NaHCO3 solutionwas added. The resulted mixture was extracted withethyl acetate, dried over MgSO4, filtered, and concentratedunder vacuum. The residue was purified by a silica gel columnusing ethyl acetate and petroleum ether as eluent to affordthe desired compound (b1-b30) as a white powder | |
In toluene at 100℃; | 2.10. General Procedure for the Preparation of Compoundsb General procedure: A selected arylcarboxylic acid (10 mmol) was solved inSOCl2 (50 mL), which was heated to 90 °C and stirred for 1-2 h until the reaction was completed. The crude product (a1-a30) was furnished after the removal of SOCl2 under reducedpressure [64-65]. To the resulting residue, 50 mL of toluenewas added and stirred for 30 min at room temperature. Thiourea(40 mmol) was subsequently added, and the reactionsolution was heated to 100 °C for 1.5-2 h [66, 67]. At the endof the reaction (monitored by TLC), the solvent was removedunder vacuum, and excess saturated NaHCO3 solutionwas added. The resulted mixture was extracted withethyl acetate, dried over MgSO4, filtered, and concentratedunder vacuum. The residue was purified by a silica gel columnusing ethyl acetate and petroleum ether as eluent to affordthe desired compound (b1-b30) as a white powder |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With ammonium hydroxide | |
79% | With ammonium hydroxide In acetone at 27℃; | |
66.4% | With 2-amino-2-hydroxymethyl-1,3-propanediol In dichloromethane at 20℃; |
With ammonia | ||
With ammonia In dichloromethane at 0 - 20℃; | ||
With ammonia In diethyl ether at 0 - 20℃; for 2h; | ||
With ammonia In dichloromethane at 0 - 20℃; for 4h; | ||
With ammonia In dichloromethane at 20 - 30℃; | benzoylthiourea [0049] The RBF was changed to include a sealed glass-fritted bubbler system connected to an ammonia gas supply and an exit bubbler-scrubber system. To the clear cold reaction mixture (controlled at a temperature below 30°C with an external ice- water bath) was slowly purged ammonia gas. During the addition, ammonia was consumed and the reaction mixture slowly became pale and cloudy/milky in appearance. The mixture was allowed to warm to room temperature, and stirring continued for an additional hour after ammonia addition ceases. Nitrogen gas was then reintroduced into the system to purge residual ammonia gas. The resulting solid is collected by vacuum filtration and washed with additional dichloromethane to provide a slightly yellow solid, which was recrystallized from ethanol. The solid was then dried to a constant weight in vacuo at a temperature of 50°C and a pressure of <1 mTorr. The resulting solid was observed to have a melting point of 171.62°C, as determined by DSC. FT-IR, ATR-Accessory, 3301-3146 can-1 (-NH2 and -NH-) , 1675 (carbonyl), 1599, 1526 and 1403 (-NCSN-), 1233 (-C-N-) . 1H NMR - DMSOd6, δ 11.1 ppm (m, singlet, -NH-) , 9.90 and 9.55 (m, doublet,- NH2) , 7.90 (s, doublet, aromatic H) , 7.60-7.40 (s, multiplet, aromatic H) , 3.65 {(, singlet, solvent exchange). 13C NMR - DMSOd6, δ 187.δ ppm (NH-CS-NH2) , 173.5 (Ar-CO-) , 139.0- 132.0 (aromatic C) . | |
With ammonia In dichloromethane at 30℃; | Benzoylthiourea The RBF was changed to include a sealed glass-fritted bubbler system connected to an ammonia gas supply and an exit bubbler-scrubber system. To the clear cold reaction mixture (controlled at a temperature below 30°C with an external ice- water bath) was slowly purged ammonia gas. During the addition, ammonia was consumed and the reaction mixture slowly became pale and cloudy/milky in appearance. The mixture was allowed to warm to room temperature, and stirring continued for an additional hour after ammonia addition ceases. Nitrogen gas was then reintroduced into the system to purge residual ammonia gas. The resulting solid is collected by vacuum filtration and washed with additional dichloromethane to provide a slightly yellow solid, which was recrystallized from ethanol. The solid was then dried to a constant weight in vacuo at a temperature of 50°C and a pressure of FT-IR, ATR-Accessory, 3301-3146 cm-1 (-NH2 and -NH-) , 1675 (carbonyl), 1599, 1526 and 1403 (-NCSN-), 1233 (-C-N-) . *H NMR - DMSOd6, δ 11.1 ppm (m, singlet, -NH-) , 9.90 and 9.55 (m, doublet,- NH2) , 7.90 (s, doublet, aromatic H) , 7.60-7.40 (s, multiplet, aromatic H) , 3.65 (s, singlet, solvent exchange). 13C NMR - DMSOd6, δ 187.5 ppm (NH-CS-NH2) , 173.5 (Ar-CO-) , 139.0- 132.0 (aromatic C) . | |
With ammonium hydroxide In chloroform Heating; | ||
With ammonia In acetone at 20℃; for 3h; | ||
With ammonia In acetone Reflux; | 2.2. General Procedures for Synthesis of BenzoylthioureasDerivatives (Series A: 1a-r, 2a-i and 3a-b; SeriesB: 4a-j, 5a-j and 6a-j) General procedure: The benzoylthioureas derivatives were synthesized accordingto the methodology described in our previous work[17]. Concisely, suitable benzoyl chloride (11 mmol) wasadded to ammonium thiocyanate (440 mmol. L-1) in dry acetone (25 mL). The reaction mixture was refluxed for 15 minand then cooled down to room temperature. After that, a solutionof appropriate amine (11 mol. L-1) in acetone wasadded and the resulting mixture was stirred under reflux forfurther 30 min. Then, the reaction mixture was poured intocrushed ice and vigorously stirred for 15 min. Each obtainedsolid product was filtered off, washed with deionized waterand then recrystallized from ethanol or ethanol in acetone.All compounds previously reported by the literature had theirpurities verified by their melting points and 1H RMN spectraanalysis. The purity of unreported compounds was also verifiedby HRMS. Full data set for the novel benzoylthioureasderivatives are listed below. | |
With ammonium hydroxide at 0 - 20℃; | ||
With ammonia at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dihydrogen peroxide In ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine In acetic acid Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium hydroxide In acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) LiH, DMF, (ii) /BRN= 969135/; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone for 1h; Heating; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In acetone for 1h; Heating; Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone for 1h; Heating; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone for 0.25h; Heating; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone for 1h; Heating; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63.7% | In ethanol for 0.25h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In acetone at 0 - 5℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | In ethanol for 0.25h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In ethanol for 0.25h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In ethanol for 0.25h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In acetone at 0 - 5℃; for 0.75h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In acetone at 0 - 5℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | In acetone at 0 - 5℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In acetone at 0 - 5℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With air at 230℃; for 10h; further identificated products isolated; analogous reaction of other thiourea derivatives; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium 1.) 30-35 deg C, 15-20 min, 2.) acetone, RT, 2.5 h, reflux, RT, 1 h; Yield given. Multistep reaction. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium methylate In methanol at 25℃; var. buffers, var. ionic strength, other reagent; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13.5% | With pyridine for 0.166667h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium methylate In methanol at 25℃; var. buffers, var. ionic strength; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In toluene at 20 - 25℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 17% 2: 7 g | In benzene for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 17% 2: 2% 3: 8% | In benzene at 50℃; for 100h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; lead acetate 1.) reflux, 5 min; 2.) 65 deg C, water, 10 min; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.2% | With polyethylene glycol-400 In dichloromethane at 20℃; | |
With p,p'-diaminobiphenyl 1.) acetone, 15 min; 2.) acetone, reflux, 1 h; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In hexane; acetonitrile at 50℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Der Hydrolyse; | ||
Ionisierung in alkalischer Loesung; | ||
Hydrolyse; |
Hydrolyse in Base; | ||
Hydrolyse in Saeure; | ||
Mono- u. Diprotonierung: UV-Sp., ε, pK-Werte; | ||
Hydrolyse in H2SO4: Kinetik, Geschw.-Konst., ΔS(excit.), E(a); | ||
Rk. mit Br2, CHCl3 (S. 1532); | ||
Umwandlung zu Benzoylisothiocyanat: k; | ||
Rk. m. prim. Aminen zu N'-substit. N-Benzoylthioharnstoffen; | ||
Rk. mit P2S5; | ||
With sodium methylate In methanol at 25℃; other reagents; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
beim Erhitzen auf den Schmelzpunkt; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 140 - 150℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | Stage #1: potassium thioacyanate; benzoyl chloride In acetone at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Heating; Stage #2: With ammonium hydroxide at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; | N-Carbamothioylbenzamide (52). Benzoyl chloride (11.5 ml, 14.05 g, 100 mmol) wasadded drop-wise to a suspension of 10.69 g potassium thiocyanate (110 mmol) in 100 mL hotacetone. The reaction was allowed to cool to room temperature and stirred for additional 30min whereupon a white precipitate was formed. The solid was filtered off and the filtrate wastreated with 50 ml 28% (w/w) aqueous ammonia solution. After stirring at room temperaturefor 30 min. the solvent was removed and the crude product was recrystallized from EtOH,yielding colorless needle-shaped crystals (9.29 g, 51.6 mmol, 52%); mp: 174 °C (lit. 173 °C);31H NMR (200 MHz, DMSO-d6) δ = 11.23 (s, 1H), 9.86 (s, 1H), 9.57 (s, 1H), 7.93 (d, J = 7.0Hz, 2H), 7.63 (t, J = 7.3 Hz, 1H), 7.50 (t, J = 7.3 Hz, 2H); 13C NMR (50 MHz, DMSO-d6) δ =182.08, 167.79, 132.97, 132.27, 128.58, 128.39 |
In acetone Heating; | ||
With ammonium hydroxide In acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | In dichloromethane at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With aluminum oxide; potassium fluoride at 100℃; for 0.333333h; microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: polyethylene glycol-400 / CH2Cl2 / 1 h / 20 °C 2: 66.4 percent / tris(hydroxymethyl)aminomethane / CH2Cl2 / 20 °C | ||
Multi-step reaction with 2 steps 1: polyethylene glycol-400 / CH2Cl2 / 1 h / 20 °C 2: 34 percent / CH2Cl2 / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetone / 0.08 h / Heating 2: acetone / 1 h / Heating | ||
Multi-step reaction with 2 steps 1: acetone / 0.08 h / Heating 2: 2.) Na / 1.) 30-35 deg C, 15-20 min, 2.) acetone, RT, 2.5 h, reflux, RT, 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: benzene 2: beim Erhitzen | ||
Multi-step reaction with 2 steps 1: dichloromethane / 10 - 39 °C / Inert atmosphere 2: ammonia / dichloromethane / 20 - 30 °C | ||
Multi-step reaction with 2 steps 1: dichloromethane / 1.33 h / 10 - 39 °C / Inert atmosphere 2: ammonia / dichloromethane / 30 °C |
Multi-step reaction with 2 steps 1: acetone / 0.25 h / Reflux 2: ammonia / acetone / 3 h / 20 °C | ||
Multi-step reaction with 2 steps 1: acetone / 1 h / 80 °C 2: ammonium hydroxide / acetone / 27 °C | ||
Multi-step reaction with 2 steps 1: acetone / 0.25 h / Reflux 2: ammonia / acetone / Reflux | ||
Multi-step reaction with 2 steps 1: acetonitrile / 2 h / 65 °C 2: ammonium hydroxide / 0 - 20 °C | ||
Multi-step reaction with 2 steps 1: ethyl acetate / 1 h / 80 °C 2: ammonia / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sodium azide; iodine; triethylamine at 20℃; for 4h; | |
Multi-step reaction with 2 steps 1: sodium azide; lead oxide 2: benzene; hydrazoic acid / unter Druck |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: diluted KOH-solution 2: benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 2: aq. HCl / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In ethanol for 2h; Inert atmosphere; Schlenk technique; Reflux; | Ethyl 2-benzamidothiazole-4-carboxylate (53). A solution of 4.5 g N-carbamothioylbenzamide(52, 25 mmol) and 4.39 ml ethyl bromopyruvat (6.83 g, 35 mmol) in 100 ml EtOHwas heated to reflux for 2 h. Then, the solvent was removed, the residue was dissolved in 350ml EtOAc, washed three times with a saturated sodium carbonate solution and two times withbrine. The organic layer was separated, concentrated to 20 ml and diluted with 100 ml nhexanewhereupon a white precipitate was formed. The solid was filtered off, yielding a whitesolid (6.48 g, 23.5 mmol, 94%); mp: 133 °C (lit. 146-147 °C);5 1H NMR (300 MHz, DMSOd6)δ = 13.04 (s, 1H), 8.13 (m, 3H), 7.65 (t, J = 7.3 Hz, 1H), 7.55 (t, J = 7.5 Hz, 2H), 4.30 (q,J = 7.1 Hz, 2H), 1.30 (t, J = 7.1 Hz, 3H); 13C NMR (75 MHz, DMSO-d6) δ = 165.51, 161.07,158.76, 141.15, 132.83, 131.55, 128.63, 128.21, 123.13, 60.63, 14.21; GC-MS (EI, 70 eV): tr(min) = 18.5; m/z (%): 77 (39), 105 (100), 248 (35), 276 (6) (M)+. |
In ethanol | 23.A A. A. N-(4-ethoxycarbonylthiazol-2-yl)benzamide A solution of 19.02 g. of benzoylthiourea and 19.12 g. of ethyl bromopyruvate in 300 ml. of ethanol was refluxed for 2 hours. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (1 liter) and 20% aqueous sodium carbonate (400 ml.). The organic layer was separated, washed successively with 20% aqueous sodium carbonate (3*400 ml.), water (2*400 ml.) and a brine solution (2*400 ml.) and dried over sodium sulfate. The solution was concentrated to about 50 ml. and the precipitated solids filtered and dried, 20.16 g., m.p. 146-147° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; water; acetone | 2 N-(Aminothioxomethyl)benzamide EXAMPLE 2 N-(Aminothioxomethyl)benzamide To a two-liter-round-bottomed flask fitted with an overhead stirrer, addition funnel and a condenser was added 400 ml of acetone and 85.0 g (1.12 moles) of ammonium thiocyanate. To this solution was added 140.6 g (1.00 moles) of benzoyl chloride. The resultant slurry was heated at reflux for 15 minutes and then the heat was removed and 200 ml of concentrated ammonium hydroxide was added at a rate to maintain reflux. The reaction mixture was heated at reflux for an additional 15 minutes and then cooled to room temperature. This mixture was added to 6 liters of water, and the resulting precipitate was collected by filtration and washed with 2 liters of water, then air dried and recrystallized from 1.5 liters of ethanol to give 98.5 g of the desired product as a white solid, mp 170°-171° C. The procedure described hereinabove and using the appropriately substituted acid chloride was used to prepare the compounds listed in Table V. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aqueous NH3 In sodium hydroxide; acetone | 21 4,6-dimethoxy-5-(2-imidazolin-2-yl)-aminopyrimidine 34 g of the N-benzoyl thiourea are boiled in 30 ml 10% NaOH for 5 minutes. After cooling, the solution is acidified with concentrated HCl and the pH-value is brought to 9 by means of a 15% aqueous NH3 solution. The precipitated crystals are vacuum dried and washed with water. 16 g (70%) N-(4,6-dimethoxy-5-pyrimidyl)-thiourea, melting point 210° C., is obtained. 16 g of this thiourea derivative are suspended in 3 l acetone and mixed with 25.5 g methyl iodide. The mixture is heated for 1 hour under reflux. After cooling, the precipitated crystals are vacuum dried, washed with acetone, and dried. 20 g (75%) of N-(4,6-dimethoxy-5-pyrimidyl)-S-methylisothiouronium iodide, melting point 215° C., is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide | 7 6,7,8,9-Tetrahydro-5H-pyrido[2,3-b]azepine-9-thiocarboxamide The benzoyl thiourea (2.7 g.) was treated with 10% aqueous sodium hydroxide solution (15 ml.) and the mixture heated at reflux for 1.5 hours. The cooled reaction mixture was filtered and the solid recrystallized from isopropanol to give the title compound as colourless needles (0.4 g.) m.p. 121°C. (Found: C, 57.7; H, 6.6; N, 20.3; C10 H13 N3 S requires: C, 57.9; H, 6.3; N, 20.3%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | In dichloromethane | P.66 Synthesis of 1-benzoyl-2-methylisothiourea hydroiodide Production Example 66 Synthesis of 1-benzoyl-2-methylisothiourea hydroiodide To a solution of N-benzoylthiourea (90 mg, 0.5 mmol) in methylene chloride (2 ml), methyl iodide (170 mg, 1.2 mmol) was added. The resultant mixture was left over at room temperature for 18 hours. The resulting crystals were collected by filtration, whereby the title compound was obtained (60 mg, 37% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In not given addn. of hot mixt. of benzoyl thiourea and pyridine (1:1 ratio) to VOSO4 soln. with constant stirring; ice cooling (4°C); collecting; washing; drying in vac.; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol Heating; | ||
In ethanol Reflux; | ||
In acetonitrile Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; potassium carbonate In ethanol for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide at 100℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate In ethanol Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dihydrogen peroxide; potassium hydroxide In methanol for 1h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 43% 2: 40% | In dichloromethane; N,N-dimethyl-formamide at 0℃; for 2h; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With tetrabutyl ammonium fluoride In chloroform at -10℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With triphenylphosphine In benzene at 27℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ethanol / 2 h / Inert atmosphere; Schlenk technique; Reflux 2: sodium hydroxide; ethanol / 4 h / 60 °C / Inert atmosphere; Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: ethanol / 2 h / Inert atmosphere; Schlenk technique; Reflux 2: sodium hydroxide; ethanol / 4 h / 60 °C / Inert atmosphere; Schlenk technique 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 14 h / 0 - 20 °C / Inert atmosphere; Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: ethanol / 2 h / Inert atmosphere; Schlenk technique; Reflux 2: sodium hydroxide; ethanol / 4 h / 60 °C / Inert atmosphere; Schlenk technique 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 14 h / 0 - 20 °C / Inert atmosphere; Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | In ethanol at 80℃; for 0.5h; Microwave irradiation; | General procedure: Studied 4-(4-chlorophenyl)thiazol-2-amines were synthesized according to the general procedure for the synthesis of 2-aminothiazole derivatives [35]. The cyclic condensation of an α-bromoketone (1eq.) and N-substituted thiourea (1eq.) in anhydrous ethanol, stirring under microwave irradiation at 80°C for 30min. The precipitating hydrobromide salts were collected and washed with water and cold ethanol. If needed, further purification was done after neutralization with saturated ammoniumhydroxide solution, stirring at room temperature, filtration of the precipitate and washing with cold ethanol. Colum chromatography on silica gel (eluent: hexane/ethylacetate 2:1 or dichloromethane/methanol 9:1) afforded the titled compounds in variable yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium hydroxide / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium hydroxide / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium hydroxide / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium hydroxide / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium hydroxide / ethanol |
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