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[ CAS No. 614-23-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 614-23-3
Chemical Structure| 614-23-3
Chemical Structure| 614-23-3
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Quality Control of [ 614-23-3 ]

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Product Details of [ 614-23-3 ]

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 :

Calculated chemistry of [ 614-23-3 ]      Expand+

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.15

Safety of [ 614-23-3 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P501-P270-P264-P301+P310+P330-P405 UN#:2811
Hazard Statements:H301 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 614-23-3 ]

* 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.

  • Downstream synthetic route of [ 614-23-3 ]

[ 614-23-3 ] Synthesis Path-Downstream   1~97

  • 1
  • [ 24442-57-7 ]
  • [ 614-23-3 ]
  • [ 13053-82-2 ]
YieldReaction ConditionsOperation in experiment
With methanol
  • 2
  • [ 614-23-3 ]
  • [ 15150-25-1 ]
YieldReaction ConditionsOperation in experiment
91% With copper(l) iodide; sodium hydroxide In dimethyl sulfoxide at 90℃; for 2.5h;
With sodium azide; lead(II) oxide
  • 3
  • [ 36029-56-8 ]
  • [ 614-23-3 ]
YieldReaction ConditionsOperation in experiment
(hydrolysis);
beim Erhitzen;
  • 4
  • [ 614-23-3 ]
  • [ 108-24-7 ]
  • [ 75-36-5 ]
  • [ 4984-27-4 ]
  • [ 65-85-0 ]
YieldReaction ConditionsOperation in experiment
at 130 - 150℃;
  • 5
  • [ 614-23-3 ]
  • [ 100-44-7 ]
  • [ 405873-41-8 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide
  • 6
  • [ 98-88-4 ]
  • [ 17356-08-0 ]
  • [ 614-23-3 ]
YieldReaction ConditionsOperation 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

  • 7
  • [ 532-55-8 ]
  • [ 614-23-3 ]
YieldReaction ConditionsOperation 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;

Reference: [1]Kavalek, Jaromir; Novak, Jaroslav; Sterba, Vojeslav [Collection of Czechoslovak Chemical Communications, 1982, vol. 47, # 10, p. 2702 - 2710]
[2]Sindhuja, Dharmalingam; Vasanthakumar, Punitharaj; Bhuvanesh, Nattamai; Karvembu, Ramasamy [European Journal of Inorganic Chemistry, 2019, vol. 2019, # 31, p. 3588 - 3596]
[3]Xu, Xiaoyong; Zhongli; Yang, Zhengyu; Chen, Gang; Qian, Xuhong [Synthetic Communications, 2003, vol. 33, # 15, p. 2585 - 2592]
[4]Miquel [Annales de Chimie (Cachan, France), 1877, vol. &lt;5&gt; 11, p. 318]
[5]Yoo, Choong Leol; Yu, Gui Jun; Yang, Baoxue; Robins, Lori I.; Verkman; Kurth, Mark J. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 8, p. 2610 - 2614]
[6]Location in patent: experimental part Lim, Herman D.; Istyastono, Enade P.; van de Stolpe, Andrea; Romeo, Giuseppe; Gobbi, Silvia; Schepers, Marjo; Lahaye, Roger; Menge, Wiro M.B.P.; Zuiderveld, Obbe P.; Jongejan, Aldo; Smits, Rogier A.; Bakker, Remko A.; Haaksma, Eric E.J.; Leurs, Rob; de Esch, Iwan J.P. [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 11, p. 3987 - 3994]
[7]Location in patent: scheme or table Mills, Aaron D.; Yoo, Choong; Butler, Jeffrey D.; Yang, Baoxue; Verkman; Kurth, Mark J. [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 1, p. 87 - 91]
[8]Current Patent Assignee: HENKEL AG &amp; CO. KGAA - WO2014/4297, 2014, A1 Location in patent: Paragraph 0049
[9]Current Patent Assignee: HENKEL AG &amp; CO. KGAA - WO2014/4309, 2014, A1 Location in patent: Paragraph 0049
[10]Zhao, Meng-Meng; Dong, Xiu-Yan; Yang, U-Hua; Li, Gang; Zhang, U-Jie [Asian Journal of Chemistry, 2014, vol. 26, # 1, p. 237 - 240]
[11]Brito, Tiago O.; Souza, Aline X.; Mota, Yane C. C.; Morais, Vinicius S. S.; De Souza, Leandro T.; De Fátima, Ângelo; Macedo, Fernando; Modolo, Luzia V. [RSC Advances, 2015, vol. 5, # 55, p. 44507 - 44515]
[12]Abreu, Lethícia O.; Bispo, Marcelle L. F.; Brito, Tiago O.; Gomes, Karen M.; Lourenço, Maria C. S.; Macedo, Fernando; Pereira, Patricia M. L.; Tisher, Cesar A.; Yamada-Ogatta, Sueli F.; de Fátima, Ângelo [Medicinal Chemistry, 2020, vol. 16, # 1, p. 93 - 103]
[13]Doble, Mukesh; Manju, S. L.; Sinha, Shweta [ACS Medicinal Chemistry Letters, 2019]
[14]Shaik, Bajivali; Seelam, Mohan; Tamminana, Ramana; Kammela, Prasad Rao [Letters in Organic Chemistry, 2021, vol. 18, # 5, p. 382 - 388]
  • 8
  • [ 504-64-3 ]
  • [ 614-23-3 ]
  • [ 28918-72-1 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile Ambient temperature;
  • 10
  • [ 614-23-3 ]
  • [ 614-22-2 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide In ethanol
  • 11
  • [ 614-23-3 ]
  • [ 53246-50-7 ]
YieldReaction ConditionsOperation in experiment
With bromine In acetic acid Heating;
  • 12
  • [ 540-72-7 ]
  • [ 98-88-4 ]
  • [ 614-23-3 ]
YieldReaction ConditionsOperation in experiment
With ammonium hydroxide In acetone
  • 14
  • [ 614-23-3 ]
  • [ 77-78-1 ]
  • [ 25508-17-2 ]
YieldReaction ConditionsOperation in experiment
In methanol; acetone
  • 15
  • [ 614-23-3 ]
  • [ 74-88-4 ]
  • [ 71389-20-3 ]
YieldReaction ConditionsOperation in experiment
(i) LiH, DMF, (ii) /BRN= 969135/; Multistep reaction;
  • 16
  • [ 2010-06-2 ]
  • [ 614-23-3 ]
  • [ 4921-87-3 ]
YieldReaction ConditionsOperation in experiment
In acetone for 1h; Heating; Yield given;
  • 17
  • [ 27182-54-3 ]
  • [ 532-55-8 ]
  • [ 614-23-3 ]
  • [ 97149-59-2 ]
YieldReaction ConditionsOperation in experiment
82% In acetone for 1h; Heating; Yields of byproduct given;
  • 18
  • [ 2103-91-5 ]
  • [ 614-23-3 ]
  • [ 112672-08-9 ]
YieldReaction ConditionsOperation in experiment
In acetone for 1h; Heating; Yield given;
  • 19
  • [ 2103-99-3 ]
  • [ 614-23-3 ]
  • [ 89012-11-3 ]
YieldReaction ConditionsOperation in experiment
In acetone for 1h; Heating;
  • 20
  • [ 2103-94-8 ]
  • [ 614-23-3 ]
  • [ 113333-06-5 ]
YieldReaction ConditionsOperation in experiment
In acetone for 0.25h; Heating; Yield given;
  • 21
  • [ 2104-04-3 ]
  • [ 614-23-3 ]
  • [ 89402-64-2 ]
YieldReaction ConditionsOperation in experiment
In acetone for 1h; Heating; Yield given;
  • 22
  • [ 614-23-3 ]
  • [ 51126-04-6 ]
  • 4-(2-benzoylamino-4-thiazolyl)-3-phenylsydnone [ No CAS ]
YieldReaction ConditionsOperation in experiment
63.7% In ethanol for 0.25h; Ambient temperature;
  • 23
  • [ 614-23-3 ]
  • [ 64119-09-1 ]
  • [ 75127-72-9 ]
YieldReaction ConditionsOperation in experiment
76% In acetone at 0 - 5℃;
  • 24
  • [ 614-23-3 ]
  • [ 76242-34-7 ]
  • C19H14N4O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% In ethanol for 0.25h; Ambient temperature;
  • 25
  • [ 614-23-3 ]
  • [ 76242-33-6 ]
  • C18H11ClN4O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In ethanol for 0.25h; Ambient temperature;
  • 26
  • [ 614-23-3 ]
  • [ 76242-35-8 ]
  • C19H14N4O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% In ethanol for 0.25h; Ambient temperature;
  • 27
  • [ 614-23-3 ]
  • [ 64119-04-6 ]
  • [ 75127-69-4 ]
YieldReaction ConditionsOperation in experiment
60% In acetone at 0 - 5℃; for 0.75h;
  • 28
  • [ 614-23-3 ]
  • [ 64119-07-9 ]
  • [ 75127-70-7 ]
YieldReaction ConditionsOperation in experiment
65% In acetone at 0 - 5℃;
  • 29
  • [ 614-23-3 ]
  • [ 64119-13-7 ]
  • [ 75127-71-8 ]
YieldReaction ConditionsOperation in experiment
50% In acetone at 0 - 5℃;
  • 30
  • [ 614-23-3 ]
  • [ 64119-10-4 ]
  • [ 75127-73-0 ]
YieldReaction ConditionsOperation in experiment
82% In acetone at 0 - 5℃;
  • 31
  • [ 4921-91-9 ]
  • [ 614-23-3 ]
  • [ 55-21-0 ]
  • [ 622-78-6 ]
  • [ 100-52-7 ]
  • [ 532-55-8 ]
  • [ 134-81-6 ]
YieldReaction ConditionsOperation in experiment
With air at 230℃; for 10h; further identificated products isolated; analogous reaction of other thiourea derivatives;
  • 32
  • [ 90559-00-5 ]
  • [ 532-55-8 ]
  • [ 614-23-3 ]
  • [ 97149-68-3 ]
YieldReaction ConditionsOperation 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;
  • 33
  • [ 74346-74-0 ]
  • [ 614-23-3 ]
  • [ 591-08-2 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate In methanol at 25℃; var. buffers, var. ionic strength, other reagent;
  • 35
  • [ 74346-73-9 ]
  • [ 614-23-3 ]
  • [ 17356-08-0 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate In methanol at 25℃; var. buffers, var. ionic strength;
  • 36
  • [ 28241-61-4 ]
  • [ 98-88-4 ]
  • [ 614-23-3 ]
YieldReaction ConditionsOperation in experiment
In acetone for 1h; Heating;
  • 37
  • [ 614-23-3 ]
  • [ 185-80-8 ]
  • [ 117840-40-1 ]
YieldReaction ConditionsOperation in experiment
75% In toluene at 20 - 25℃; for 4h;
  • 38
  • [ 1113-62-8 ]
  • [ 532-55-8 ]
  • [ 614-23-3 ]
  • [ 85741-87-3 ]
YieldReaction ConditionsOperation in experiment
1: 17% 2: 7 g In benzene for 24h;
  • 39
  • [ 95512-60-0 ]
  • [ 532-55-8 ]
  • [ 614-23-3 ]
  • 6-methyl-5-nitro-2-phenyl-4(1H)-pyrimidinethione [ No CAS ]
  • N-benzoyl-3-amino-2-nitro-2-butenethioamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 17% 2: 2% 3: 8% In benzene at 50℃; for 100h;
  • 40
  • [ 614-23-3 ]
  • N,N'-dicyano-4,4'-diaminobiphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; lead acetate 1.) reflux, 5 min; 2.) 65 deg C, water, 10 min; Yield given. Multistep reaction;
  • 41
  • [ 1147550-11-5 ]
  • [ 98-88-4 ]
  • [ 614-23-3 ]
YieldReaction ConditionsOperation 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;
  • 42
  • [ 614-23-3 ]
  • [ 187806-29-7 ]
  • 1-Benzoyl-2-[6-hydroxy-2,7,8-trimethyl-2-(4,8,12-trimethyl-tridecyl)-chroman-5-ylmethyl]-isothiourea; hydrobromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% In hexane; acetonitrile at 50℃; for 2h;
YieldReaction ConditionsOperation 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;

YieldReaction ConditionsOperation in experiment
beim Erhitzen auf den Schmelzpunkt;
  • 49
  • [ 614-23-3 ]
  • [ 100-44-7 ]
  • [ 405873-41-8 ]
  • 50
  • [ 614-23-3 ]
  • [ 7664-41-7 ]
  • [ 113-00-8 ]
  • 51
  • [ 614-23-3 ]
  • [ 7732-18-5 ]
  • [ 124-38-9 ]
  • [ 7783-06-4 ]
  • [ 7664-41-7 ]
  • [ 65-85-0 ]
YieldReaction ConditionsOperation in experiment
at 140 - 150℃;
  • 52
  • [ 7647-01-0 ]
  • <i>N</i>-benzoylthiocarbamoyl-benzimidic acid isobutyl ester [ No CAS ]
  • [ 614-23-3 ]
  • 53
  • [ 333-20-0 ]
  • [ 98-88-4 ]
  • [ 614-23-3 ]
YieldReaction ConditionsOperation 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
  • 54
  • [ 75-64-9 ]
  • [ 532-55-8 ]
  • [ 614-23-3 ]
  • [ 22283-39-2 ]
YieldReaction ConditionsOperation in experiment
34% In dichloromethane at 20℃; for 0.5h;
  • 55
  • [ 614-23-3 ]
  • [ 100-46-9 ]
  • 1-benzoyl-3-benzylguanidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With aluminum oxide; potassium fluoride at 100℃; for 0.333333h; microwave irradiation;
  • 56
  • [ 98-88-4 ]
  • [ 614-23-3 ]
YieldReaction ConditionsOperation 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
  • 57
  • [ 98-88-4 ]
  • [ 614-23-3 ]
YieldReaction ConditionsOperation 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
  • 58
  • [ 98-88-4 ]
  • [ 614-23-3 ]
YieldReaction ConditionsOperation 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

  • 59
  • [ 614-23-3 ]
  • [ 4847-62-5 ]
YieldReaction ConditionsOperation 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
  • 60
  • [ 614-23-3 ]
  • [ 124882-44-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diluted KOH-solution 2: benzene
  • 61
  • [ 614-23-3 ]
  • [ 65358-77-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: aq. HCl / Heating
  • 62
  • [ 70-23-5 ]
  • [ 614-23-3 ]
  • ethyl 2-benzamidothiazole-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 63
  • ammonium thiocyanate [ No CAS ]
  • [ 1336-21-6 ]
  • [ 98-88-4 ]
  • [ 614-23-3 ]
YieldReaction ConditionsOperation 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.
  • 64
  • N-(4,6-dimethoxy-5-pyrimidyl)-thiourea [ No CAS ]
  • [ 614-23-3 ]
  • [ 74-88-4 ]
  • [ 75438-82-3 ]
YieldReaction ConditionsOperation 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.
  • 65
  • [ 614-23-3 ]
  • [ 60782-43-6 ]
YieldReaction ConditionsOperation 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%).
  • 66
  • [ 614-23-3 ]
  • [ 74-88-4 ]
  • [ 6966-84-3 ]
YieldReaction ConditionsOperation 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).
  • 67
  • vanadyl(IV) sulfate dihydrate [ No CAS ]
  • [ 614-23-3 ]
  • [oxovanadium(IV) (pyridine) (benzoyl thiourea)0.5 sulphate]2 [ No CAS ]
YieldReaction ConditionsOperation 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.;
  • 70
  • [ 614-23-3 ]
  • [ 35158-39-5 ]
  • 2-benzoylamino-4-(4-chlorophenyl)-thiazole-5-acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 100℃; Microwave irradiation;
  • 71
  • [ 614-23-3 ]
  • [ 70386-38-8 ]
  • C20H15N3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate In ethanol Reflux;
  • 72
  • uranyl nirate hexahydrate [ No CAS ]
  • [ 614-23-3 ]
  • [ 1421634-94-7 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide; potassium hydroxide In methanol for 1h; Reflux;
  • 73
  • [ 614-23-3 ]
  • [ 916597-44-9 ]
  • [ 1450899-58-7 ]
  • [ 1450899-75-8 ]
YieldReaction ConditionsOperation in experiment
1: 43% 2: 40% In dichloromethane; N,N-dimethyl-formamide at 0℃; for 2h; stereoselective reaction;
  • 74
  • [ 6061-04-7 ]
  • [ 614-23-3 ]
  • (Z)-N-(5-(nitromethylene)-1,4,2-dithiazol-3-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With tetrabutyl ammonium fluoride In chloroform at -10℃;
  • 75
  • bis(μ2-chloro)-tris(triphenylphosphine)-di-copper(I) complex [ No CAS ]
  • [ 614-23-3 ]
  • CuCl(N-carbamothioylbenzamide)(PPh<SUB>3</SUB>)<SUB>2</SUB> [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With triphenylphosphine In benzene at 27℃;
  • 76
  • [ 614-23-3 ]
  • 2-benzamidothiazole-4-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation 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
  • 77
  • [ 614-23-3 ]
  • N-(4-(4-phenylpiperazine-1-carbonyl)thiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation 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
  • 78
  • [ 614-23-3 ]
  • N-(4-(4-(3,5-bis(trifluoromethyl)phenyl)piperazine-1-carbonyl)thiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation 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
  • 79
  • [ 614-23-3 ]
  • [ 536-38-9 ]
  • [ 87637-30-7 ]
YieldReaction ConditionsOperation 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.
  • 80
  • [ 614-23-3 ]
  • (E)-N-(5-cinnamoyl-4-methylthiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium hydroxide / ethanol
  • 81
  • [ 614-23-3 ]
  • (E)-N-(5-(3-(4-fluorophenyl)acryloyl)-4-methylthiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium hydroxide / ethanol
  • 82
  • [ 614-23-3 ]
  • (E)-N-(5-(3-(4-chlorophenyl)acryloyl)-4-methylthiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium hydroxide / ethanol
  • 83
  • [ 614-23-3 ]
  • (E)-N-(5-(3-(4-bromophenyl)acryloyl)-4-methylthiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium hydroxide / ethanol
  • 84
  • [ 614-23-3 ]
  • (E)-N-(5-(3-(3-bromophenyl)acryloyl)-4-methylthiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium hydroxide / ethanol
  • 85
  • [ 614-23-3 ]
  • (E)-N-(4-methyl-5-(3-(3-nitrophenyl)acryloyl)thiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium hydroxide / ethanol
  • 86
  • [ 614-23-3 ]
  • (E)-N-(5-(3-(4-methoxyphenyl)acryloyl)-4-methylthiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium hydroxide / ethanol
  • 87
  • [ 614-23-3 ]
  • (E)-N-(5-(3-(3,4-dimethoxyphenyl)acryloyl)-4-methylthiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium hydroxide / ethanol
  • 88
  • [ 614-23-3 ]
  • (E)-N-(4-methyl-5-(3-(3,4,5-trimethoxyphenyl)acryloyl)thiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium hydroxide / ethanol
  • 89
  • [ 614-23-3 ]
  • (E)-N-(4-methyl-5-(3-p-tolylacryloyl)thiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium hydroxide / ethanol
  • 90
  • [ 614-23-3 ]
  • (E)-N-(5-(3-(4-(dimethylamino)phenyl)acryloyl)-4-methylthiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium hydroxide / ethanol
  • 91
  • [ 614-23-3 ]
  • (E)-N-(5-(3-(furan-2-yl)acryloyl)-4-methylthiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium hydroxide / ethanol
  • 92
  • [ 614-23-3 ]
  • (E)-N-(4-methyl-5-(3-(thiophen-2-yl)acryloyl)thiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium hydroxide / ethanol
  • 93
  • [ 614-23-3 ]
  • C36H26Cl2N12O8S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetone / 4 h / Cooling with ice 2: hydrogenchloride / water / 4 h / 40 - 45 °C / pH 6 - 6.5
  • 94
  • [ 108-77-0 ]
  • [ 614-23-3 ]
  • C11H7Cl2N5OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In acetone for 4h; Cooling with ice;
  • 95
  • [ 52462-29-0 ]
  • [ 614-23-3 ]
  • C18H22Cl2N2ORuS [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In toluene at 27℃; 2.2. Synthesis of the Ru complexes A mixture of [RuCl 2 ( 6 - p -cymene)] 2 (0.2 mmol, 122.4 mg) and ligand (L1-L5) (68-99 mg, 0.4 mmol) in toluene (30 mL) was stirred for 6-9 h at 27 °C. The reaction mixture was concentrated, and hexane was added to get orange coloured precipitate. The obtained complex was filtered, washed with hexane and diethyl ether, and dried in vacuo .
  • 96
  • [ 614-23-3 ]
  • [ 3166-00-5 ]
YieldReaction ConditionsOperation in experiment
89% With ammonia; iodine; triethylamine at 20℃; for 4h;
  • 97
  • [ 65-85-0 ]
  • [ 614-23-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / 90 °C 2: toluene / 100 °C
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