2293-07-4|1-(4-Methoxyphenyl)thiourea| Ambeed

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Structure of 2293-07-4

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Quality Control of [ 2293-07-4 ] Purity: 98% SDS Specification

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Product Details of [ 2293-07-4 ]

CAS No. :	2293-07-4
Formula :	C₈H₁₀N₂OS
M.W :	182.24
SMILES Code :	S=C(N)NC1=CC=C(OC)C=C1
MDL No. :	MFCD00004936
InChI Key :	SRYLJBWDZZMDSK-UHFFFAOYSA-N
Pubchem ID :	667549

Safety of [ 2293-07-4 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301
Precautionary Statements:	P301+P310
Class:	6.1
UN#:	2811
Packing Group:	Ⅲ

Application In Synthesis of [ 2293-07-4 ]

* 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 [ 2293-07-4 ]

[ 2293-07-4 ] Synthesis Path-Downstream 1~54

1
[ 21258-08-2 ]
[ 2293-07-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In tetrahydrofuran; water; at 100℃; for 1h;	General procedure: A solution of N-aryl-N'-benzoylthiourea (D) in aqueous sodium hydroxide (2 M)/THF (1:1) was heated to 100 C for 1 h. The precipitating solid N-substituted thiourea (E) was collected and washed with H2O.30

References: [1]Synthesis,1988,p. 456 - 459.
[2]Tetrahedron Letters,2005,vol. 46,p. 5841 - 5843.
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 228 - 233.
[4]Journal of Medicinal Chemistry,1997,vol. 40,p. 1901 - 1905.
[5]European Journal of Medicinal Chemistry,2003,vol. 38,p. 313 - 318.
[6]Journal of Medicinal Chemistry,2006,vol. 49,p. 5769 - 5776.
[7]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2991 - 2993.
[8]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 156 - 167.
[9]Archiv der Pharmazie,2013,vol. 346,p. 891 - 900.
[10]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5354 - 5367.
[11]MedChemComm,2016,vol. 7,p. 1768 - 1774.
[12]MedChemComm,2017,vol. 8,p. 2060 - 2066.
[13]MedChemComm,2018,vol. 9,p. 995 - 1010.
[14]RSC Advances,2018,vol. 8,p. 27631 - 27644.

2
[ 333-20-0 ]
[ 104-94-9 ]
[ 2293-07-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; at 80℃;	General procedure: Substituted aniline’s (1 g, 0.0107 mmol) and potassiumthiocyante (4.17 g, 0.043 mmol) were dissolved in 10 mlof conc.HCl and the mixture was refluxed for overnight at80 C. The completion of the reaction was monitored byTLC. The solid formed was filtered, dried and recrystallizedusing ethanol to obtain the required thiourea with 78-80%yield (Hantzsch and Weber 1887).

References: [1]Journal of the Indian Chemical Society,1989,vol. 66,p. 39 - 41.
[2]Medicinal Chemistry Research,2020,vol. 29,p. 442 - 458.
[3]Journal of Heterocyclic Chemistry,2020,vol. 57,p. 1573 - 1587.
[4],2020,vol. 11,p. 411 - 418.

3
[ 622-34-4 ]
[ 2293-07-4 ]
N-phenylformamidino-N-p-methoxyphenylthiocarbamide hydrochloride [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 792 - 794.

4
[ 65195-61-1 ]
[ 2293-07-4 ]
C₁₆H₁₈N₄O₂S*ClH [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 792 - 794.

5
[ 2293-07-4 ]
[ 74-88-4 ]
[ 27806-85-5 ]

References: [1]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 2539 - 2542.
[2]European Journal of Medicinal Chemistry,1990,vol. 25,p. 81 - 85.

6
[ 2293-07-4 ]
[ 74-88-4 ]
[ 27806-85-5 ]

References: [1]Synthesis,1980,p. 60 - 63.
[2]Zeitschrift fur Physikalische Chemie (Leipzig),1984,vol. 265,p. 849 - 864.
[3]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 156 - 167.
[4]Patent: US9212151,2015,B2 .Location in patent: Page/Page column 93-94.

7
[ 105-36-2 ]
[ 2293-07-4 ]
[ 27052-12-6 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5769 - 5776.
[2]Pharmaceuticals,2021,vol. 14.

8
[ 104-94-9 ]
[ 2293-07-4 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5769 - 5776.
[2]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 2025 - 2034.
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 228 - 233.
[4]Journal of the Chemical Society,1924,vol. 125,p. 1704.
[5]Journal of the Chemical Society,1927,p. 440.
[6]Medicinal Chemistry Research,2013,vol. 22,p. 4211 - 4222.
[7]Journal of Medicinal Chemistry,2015,vol. 58,p. 1123 - 1139.
[8]Patent: US9212151,2015,B2 .
[9]Green Chemistry,2016,vol. 18,p. 2666 - 2674.
[10]MedChemComm,2016,vol. 7,p. 1768 - 1774.
[11]Tetrahedron Letters,2016,vol. 57,p. 5297 - 5300.
[12]PLoS ONE,2017,vol. 12.
[13]MedChemComm,2018,vol. 9,p. 995 - 1010.

9
[ 6221-13-2 ]
[ 2293-07-4 ]
[ 61889-63-2 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 3.0 g (15 mmol) 4-(2-bromo)acetylpyridine (6-2) in 50 mL water was added an equimolar amount of 4-methoxyphenylthiourea (7-1; 2.75 g). The reaction was diluted with 20 mL EtOH. The reaction was allowed to stir at rt overnight, over which time a color change occurred from clear to a thick orange precipitate. The reaction mixture was diluted with 100 mL water then the pH was adjusted to neutral with 1N NaOH. The reaction was allowed to stir at rt and a large amount of precipitate formed which was collected by filtration. The resulting powder was dried under high vacuum to yield N-(4-methoxyphenyl)-4-pyridin-4-yl-1,3-thiazol-2-amine (7-2): 1H NMR (500 MHz, CD3OD) δ 8.98 (d, J=3 Hz, 2H), 8.10 (d, J=3 Hz, 2H), 7.53 (s, 1H), 3.0 (s, 3H): MS 284.3 found 284.2 (M+H+).

References: [1]Patent: US2005/176776,2005,A1 .Location in patent: Page/Page column 21.

10
[ 119-53-9 ]
[ 2293-07-4 ]
[ 79713-63-6 ]

Yield	Reaction Conditions	Operation in experiment
52%	In N,N-dimethyl-formamide; at 20℃; for 49h;Heating / reflux;	A mixture of 10 (11.66 g, 55 mmol) and 11 (10 g, 55 mmol) in DMF (30 ml) was heated to reflux for 1 h allowed to stand at RT for 48 h. A solid formed which was collected by filtration and washed with ethanol and hexane to give 12 (10.4 g, 52%) as a white solid. Mass spec: m/z 359 (MH+).

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2007,vol. 46,p. 1549 - 1553.
[2]Patent: US2006/166960,2006,A1 .Location in patent: Page/Page column 21.

11
[ 29269-45-2 ]
[ 180386-89-4 ]
[ 2293-07-4 ]
2-amino-1-cyclohexyl-1,4-dihydro-6-methyl-4-pyrimidinone hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	In ethanol;	There was thus obtained 2-amino-1-cyclohexyl-1,4-dihydro-6 -methyl-4-pyrimidinone hydrochloride (0.98 g, 30% based on thioxo compound), m.p. 225-226 C., with a satisfactory microanalysis. The starting material for Ex. 7 was prepared as follows: N-(4-Methoxyphenyl)thiourea (18.2 g, 100 mM) and 2,6,6-trimethyl-1,3-dioxin-4-one (21.3 g, 150 mM) were heated together at 140 C. (bath temperature) for 30 minutes. The solid product was cooled, treated with ethanol (100 ml), boiled for 10 minutes, cooled and the solid product was isolated by filtration. More dioxinone (21.3 g) was added to the above material and the mixture was heated at 140 C. for a further 20 minutes.

References: [1]Patent: US5223505,1993,A .

12
ammonium [ No CAS ]
aqueous sodium bisulfate [ No CAS ]
[ 104-94-9 ]
[ 2293-07-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride;	EXAMPLE 1 738 Parts of p-anisidine, 502 parts of ammonium rhodanide and 78 parts of a 40% aqueous sodium bisulfate solution are introduced successively, while stirring, into 1050 parts of 20% aqueous hydrochloric acid. This mixture is heated to 95 to 100 C. and stirred for 12 to 15 hours at this temperature. Thereafter the precipitate having been formed is filtered off with suction, while hot, washed with hot water until neutral and dried. 1038 Parts (corresponding to 95.1% of the theory) of 4-methoxyphenyl thiourea of the formula STR3 are obtained, the compound having a melting point of from 200 to 201 C. If the ammonium rhodanide is replaced by an equivalent amount of sodium or potassium rhodanide, the 4-methoxyphenyl thiourea is obtained in an equally high yield and quality.

References: [1]Patent: US4234513,1980,A .

13
ammonium thiocyanate [ No CAS ]
[ 104-94-9 ]
[ 2293-07-4 ]

References: [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 787 - 797.
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2610 - 2614.
[3]Journal of Medicinal Chemistry,2008,vol. 51,p. 1242 - 1251.

14
[ 105-39-5 ]
[ 2293-07-4 ]
[ 66625-28-3 ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 1242 - 1251.

15
[ 5349-17-7 ]
[ 2293-07-4 ]
[ 61889-63-2 ]

Yield	Reaction Conditions	Operation in experiment
78%	In neat (no solvent); for 0.0833333h;Microwave irradiation; Heating;	General procedure: Microwave method: Equimolar quantities of 4-(bromomethyl)pyridinehydrobromide (2 mmol) and substituted N-phenylthiourea (2mmol) are mixed and MW irradiated at 120 C with a power of 300 W foran optimal reaction time. After the reaction was completed, the crudemixture was cooled to 50 C before being suspended in water andalkalinized with NH4OH. To get the desired thiazole derivatives (3a-g),the precipitate was filtered and recrystallized from ethanol.
60%		[0244] 7V-(4-Methoxyphenyl)-4-(4-pyridinyl)-l,3-thiazol-2-amine (27). A mixture of bromoketone hydrobromide 1 (1.26 g, 4.50 mmol) and 4- methoxyphenylthiourea (26) (0.82 g, 4.50 mmol) in EtOH (20 mL) was stirred at reflux temperature for 1 h. The mixture was cooled to 20 0C, diluted with water (50 mL), the pH adjusted to ca. 8 with aqueous NH3 and the mixture stirred at 5 0C for 2 h. The precipitate was filtered, washed with water (5 mL) and dried. The crude solid was purified by column chromatography, eluting with EtOAc, to give amine 27 (0.76 g, 60%) as a cream powder: mp (EtOAc) 178-180 0C; 1H NMR δ 10.13 (br s, 1 H, NH), 8.61 (dd, J= 4.5, 1.6 Hz, 2 H, H-2', H-6'), 7.83 (dd, J= 4.5, 1.6 Hz, 2 H, H-3', H-5'), 7.60 (m, 3 H, H-5, H-3", H-5"), 6.95 (ddd, J= 6.8, 3.5, 2.2 Hz, 2 H, H-2", H-6"), 3.74 (s, 3 H, OCH3); 13C NMR δ 164.1, 154.2, 150.0 (2), 147.6, 141.0, 134.4, 119.8 (2), 118.7 (2), 114.2 (2), 106.6, 55.1; MS m/z 284.5 (MH+, 100%). Anal, calcd for Ci5Hi3N3OS: C, 63.58; H, 4.62; N, 14.83. Found: C, 63.45; H, 4.65; N, 14.82%.

References: [1]Journal of the Indian Chemical Society,2022,vol. 99.
[2]Patent: WO2009/114552,2009,A1 .Location in patent: Page/Page column 91.

16
[ 1227465-11-3 ]
[ 2293-07-4 ]
[ 1227465-07-7 ]

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,2010,vol. 185,p. 368 - 376.

17
[ 79-04-9 ]
[ 2293-07-4 ]
1-(4-methoxyphenyl)-2-thiohydantoin [ No CAS ]

References: [1]Journal of Sulfur Chemistry,2010,vol. 31,p. 161 - 167.

18
[ 43009-18-3 ]
[ 2293-07-4 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; copper(ll) bromide; In water; ethyl acetate; at 25℃; for 3h;	To a stirred mixture of solvent (6 mL), aqueous ammonia(2.2 mmol, 25%) and dithiocarbamic acid salt 1 (1 mmol), CuBr2 (0.5 mmol) was added slowly, and the reaction mixture was stirred at room temperature for 3 h, thioureas (2) were generated in situ. During this period, a black precipitate was observed and settled at the bottom of the roundbottom flask. The reaction mixture was transferred into centrifuged tubes and the mixture was centrifuged for 10 min by using a centrifugation machine. The black solid settled in the bottom of the centrifuge tubes. Excess ammonia was removed by heating the reaction mixture on a hot-waterbath (50 C) for 10 min. Then CuBr2 (2.2 mmol) and ketone (3, 1.1 mmol) was added and continue reflux. The progress of the reaction was investigated by TLC (2% ethyl acetate in hexane). After finishing the reaction, the reaction mixture was filtered at 50 C and the filter was extracted with ethylacetate (220 mL). The ethyl acetate layer was washed witha saturated solution of NaHCO3 (5 mL), dried over anhydrous Na2SO4, concentrated under reduced pressure, and purified over a silica-gel column (hexane - EtOAc, 9:1:) to give 2-Aminothiazoles 4a-4m.

References: [1]Synthetic Communications,2011,vol. 41,p. 792 - 805.
[2]Synthetic Communications,2012,vol. 42,p. 951 - 958.
[3]PLoS ONE,2017,vol. 12.
[4]Acta Chimica Slovenica,2017,vol. 64,p. 832 - 841.
[5]Phosphorus, Sulfur and Silicon and the Related Elements,2019,vol. 194,p. 1134 - 1139.

19
[ 98-86-2 ]
[ 2293-07-4 ]
[ 1843-15-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With carbon tetrabromide; triethylamine; In acetonitrile; at 20℃; for 2h;	General procedure: To a mixture of ketone (0.5 mmol), thiourea (0.5 mmol), and triethylamine (0.5 mmol) in acetonitrile (3 mL) was added carbon tetrabromide (0.5 mmol) in a round bottom flask at room temperature and the reaction mixture was stirred for 2-6 h. After completion of the reaction (monitored by TLC), water (5 mL) was added and the mixture was extracted with EtOAc (3*5 mL). The combined organic phase was dried over MgSO4, filtered, and evaporated under reduced pressure to give the crude product. The resulting product was purified by silica gel column chromatography using a gradient mixture of hexane/ethyl acetate as eluent to afford an analytically pure sample of 3.
	With copper(ll) bromide; In water; ethyl acetate; for 3h;Reflux;	To a stirred mixture of solvent (6 mL), aqueous ammonia(2.2 mmol, 25%) and dithiocarbamic acid salt 1 (1 mmol), CuBr2 (0.5 mmol) was added slowly, and the reaction mixture was stirred at room temperature for 3 h, thioureas (2) were generated in situ. During this period, a black precipitate was observed and settled at the bottom of the roundbottom flask. The reaction mixture was transferred into centrifuged tubes and the mixture was centrifuged for 10 min by using a centrifugation machine. The black solid settled in the bottom of the centrifuge tubes. Excess ammonia was removed by heating the reaction mixture on a hot-waterbath (50 C) for 10 min. Then CuBr2 (2.2 mmol) and ketone (3, 1.1 mmol) was added and continue reflux. The progress of the reaction was investigated by TLC (2% ethyl acetate in hexane). After finishing the reaction, the reaction mixture was filtered at 50 C and the filter was extracted with ethylacetate (220 mL). The ethyl acetate layer was washed witha saturated solution of NaHCO3 (5 mL), dried over anhydrous Na2SO4, concentrated under reduced pressure, and purified over a silica-gel column (hexane - EtOAc, 9:1:) to give 2-Aminothiazoles 4a-4m.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 5623 - 5627.
[2]Synthetic Communications,2011,vol. 41,p. 792 - 805.
[3]Phosphorus, Sulfur and Silicon and the Related Elements,2019,vol. 194,p. 1134 - 1139.

20
[ 2293-07-4 ]
[ 1566-42-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	With trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane; water; potassium hydroxide; In acetonitrile; at 20℃; for 0.166667h;	To a stirred solution of phenylthiourea 1 (1mmol) and 5% aq. KOH (5 mL) in acetonitrile (5 mL) was added DHPDMDO (0.332 g, 2mmol). The resulting mixture was allowed to stir at room temperature for an appropriate time (Table 2). After completion of the reaction as monitored by TLC, the reaction mixture was diluted with water (10mL) and the product was extracted in dichloromethan (3×5mL). The combined organic layer was washed with water (2×5mL) and dried over anhydrous Na2SO4. Evaporation of the solvent under reduced pressure gave almost pure products. Structures of the known products were established on the basis of their physical and spectroscopic (IR, 1H-NMR and 13C-NMR) data, which were consistent with those reported.[34,61]

References: [1]Journal of Sulfur Chemistry,2016,vol. 37,p. 1 - 13.
[2]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,2010,vol. 49,p. 1483 - 1487.
[3]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,2014,vol. 53,p. 174 - 178.

21
[ 24829-91-2 ]
[ 2293-07-4 ]
[ 1314243-63-4 ]

Yield	Reaction Conditions	Operation in experiment
49%	In ethanol; for 15h;Reflux;	General procedure: A mixture of 3-bromocyclohexane-1,2-dione 3 (50 mg, 0.26 mmol) and pyridine-4-carbothioamide (24.1 mg, 0.17 mmol) in EtOH (0.69 mL) was heated to reflux and stirred for 15 h. The reaction mixture was diluted with DMSO (0.5 mL) to completely dissolve all solids and the resulting mixture was purified by directly injecting the reaction mixture into a preparatory HPLC (C18, water/acetonitrile/ammonium acetate buffer) to give 2-(pyridin-4-yl)-6,7-dihydrobenzo[d]thiazol-4(5H)-one (30.4 mg, 0.13 mmol, 76%) (Table 1, entry 1).

References: [1]Tetrahedron Letters,2011,vol. 52,p. 3633 - 3635.

22
[ 3249-68-1 ]
[ 2293-07-4 ]
[ 929561-70-6 ]

Yield	Reaction Conditions	Operation in experiment
		Example B20Preparation of Compound 102; Sulfuryl chloride (0.0055 mol) was added dropwise to a solution of 3-oxo-hexanoic acid, ethyl ester (0.0055 mol) in CH2Cl2 (q.s.). The reaction mixture was stirred for 2 hours at room temperature. The solvent was evaporated. A solution of (4-methoxyphenyl)-thiourea (0.0055 mol) in EtOH (100 ml) was added to the residue. The resultant reaction mixture was stirred and refluxed for 4 hours. A saturated aqueous NaHCO3 solution was added. This mixture was extracted with EtOAc. The separated organic layer was purified by column chromatography over silica gel. The product fractions were collected and the solvent was evaporated, yielding compound 102.

References: [1]Patent: US2011/269748,2011,A1 .Location in patent: Page/Page column 42.

23
[ 672323-13-6 ]
[ 2293-07-4 ]
[ 929561-87-5 ]

Yield	Reaction Conditions	Operation in experiment
54%		Example B22Preparation of compound 104; β-Oxo-1-[(phenylmethoxy)carbonyl]-3-piperidinepropanoic acid, ethyl ester (0.0033 mol) and sulfuryl chloride (0.0036 mol) were dissolved in CH2Cl2 (10 ml). The reaction mixture was stirred for 2 hours. The solvent was evaporated in vacuo. This residue and (4-methoxyphenyl)-thiourea (0.0030 mol) were dissolved in EtOH (10 ml) and the resultant reaction mixture was stirred and refluxed for 4 hours, then cooled to room temperature. The mixture was filtered and the filter residue was washed with EtOH (10 ml), then stirred in a saturated aqueous NaHCO3 solution, then filtered off and dried in vacuo, yielding 0.8 g (54%) of compound 104.

References: [1]Patent: US2011/269748,2011,A1 .Location in patent: Page/Page column 44.

24
[ 929562-50-5 ]
[ 2293-07-4 ]
[ 929562-51-6 ]

Yield	Reaction Conditions	Operation in experiment
24%		e) Preparation of Intermediate 37; A mixture of intermediate 36 (0.00018 mol) and N,N,N-tributyl-1-butanaminium (tribromide) (0.00078 mol) in THF (20 ml) was refluxed for 2 hours. The solvent was evaporated. (4-Methoxyphenyl)-thiourea (0.00117 mol) and EtOH (20 ml) were added to the residue and then refluxed for 2 hours. The solvent was evaporated. The residue was partitioned between NaHCO3 saturated aqueous solution and EtOAc. The separated organic layer's solvent was evaporated. The residue was purified by TLC (eluens: petroleum ether/EtOAc 2:1), yielding 0.080 g (24%) of intermediate 37.

References: [1]Patent: US2011/269748,2011,A1 .Location in patent: Page/Page column 29-30.

25
[ 70-11-1 ]
[ 2293-07-4 ]
[ 1843-15-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine; In ethanol;Reflux;	25 mL solanes were added with 1 mmol of N-(4-methoxyphenyl) thiourea.1.05 mmol alpha-bromoacetophenone,10 mL of ethanol was added to dissolve, and then 1.5 mmoL of triethylamine was added and refluxed.After TLC tracks the reaction,The temperature of the reaction solution was lowered to room temperature, and the solvent was distilled off under reduced pressure.Column chromatography of the residue (eluent: petroleum ether-ethyl acetate) yields the target compound,It is a white solid with a yield of 76%.

References: [1]Catalysis Letters,2012,vol. 142,p. 1369 - 1375.
[2]Journal of Sulfur Chemistry,2011,vol. 32,p. 37 - 44.
[3]Patent: CN107629022,2018,A .Location in patent: Paragraph 0378; 0381; 0382; 0383.
[4]European Journal of Organic Chemistry,2021,vol. 2021,p. 3587 - 3597.

26
[ 619-41-0 ]
[ 2293-07-4 ]
[ 406469-94-1 ]