30709-67-2|2-Amino-5-methyl-4-phenylthiazole| Ambeed

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Quality Control of [ 30709-67-2 ] Purity: 98% SDS Specification

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Product Details of [ 30709-67-2 ]

CAS No. :	30709-67-2
Formula :	C₁₀H₁₀N₂S
M.W :	190.26
SMILES Code :	CC1=C(C2=CC=CC=C2)N=C(N)S1
MDL No. :	MFCD00617257
InChI Key :	HTXQOROHFFYFMC-UHFFFAOYSA-N
Pubchem ID :	96129

Safety of [ 30709-67-2 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H315-H318-H335
Precautionary Statements:	P261-P280-P305+P351+P338
Class:	8
UN#:	3259
Packing Group:	Ⅲ

Application In Synthesis of [ 30709-67-2 ]

* 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 [ 30709-67-2 ]

[ 30709-67-2 ] Synthesis Path-Downstream 1~35

1
[ 30709-67-2 ]
[ 121-60-8 ]
N-acetyl-sulfanilic acid-(5-methyl-4-phenyl-thiazol-2-ylamide) [ No CAS ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1948,vol. 68,p. 105,107, 108.
Chem.Abstr.,1953,p. 7453.
[2]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1948,vol. 68,p. 105,107, 108.
Chem.Abstr.,1953,p. 7453.

2
[ 23022-83-5 ]
[ 17356-08-0 ]
[ 30709-67-2 ]

References: [1]Gazzetta Chimica Italiana,1948,vol. 78,p. 681,682.

3
[ 4773-35-7 ]
[ 17356-08-0 ]
[ 30709-67-2 ]

References: [1]Bulletin de la Societe Chimique de France,1950,p. 582.

4
[ 17356-08-0 ]
[ 93-55-0 ]
[ 30709-67-2 ]

Yield	Reaction Conditions	Operation in experiment
40%	With iodine; In dimethyl sulfoxide; at 80℃; for 12h;	The reaction tube fitted with a magnetic stir propiophenone was added 0.537g (4mmol),Thiourea 0.152g (2mmol),0.051 g (0.4 mmol) of iodine and 4 ml of DMSO.Place the reaction tube in an oil bath at 80 C.The reaction was stirred for 12 h.After the reaction, the reaction solution was treated with a saturated NaHCO3 solution (20 mL).An additional 30 ml of water was added and extracted three times with 20 mL of ethyl acetate.The extract was washed with water and saturated NaCl solution, and dried over anhydrous Na2SO4.The solvent was removed under reduced pressure on a rotary evaporator, and the residue was separated by silica gel column chromatography.Eluted with petroleum ether / ethyl acetate (5: 1 by volume),To give the 2-amino-4-phenyl-5-methylthiazole product (0.152 g),The yield was 40.0%.
40%	With iodine; toluene-4-sulfonic acid; dimethyl sulfoxide; at 80℃; for 12h;Schlenk technique;	General procedure: A Schlenk tube (20 mL) was charged with ketone 1 (4 mmol),thiourea (2) (2 mmol), I2 (0.4 mmol) and DMSO (4 mL). Thetube was sealed with a rubber septum and the reaction mixturewas stirred at 80 C for 12 h. After completion of thereaction, the mixture was cooled to room temperature. Ethylacetate (20 mL) and a saturated solution of NaHCO3 (20 mL)were added and the organic layer was separated. The aqueousphase was extracted with ethyl acetate (3 × 10 mL). Thecombined organic layer was washed with a saturated solutionof NaCl (20 mL) and then dried over anhydrous Na2SO4.After filtration, the solvent was removed under reduced pressure.The crude mixture was purified by chromatography onsilica gel to yield the desired products.

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 966.
[2]Patent: CN110845437,2020,A .Location in patent: Paragraph 0120-0125.
[3]Journal of Chemical Research,2021,vol. 45,p. 89 - 94.
[4]Journal of the American Chemical Society,1945,vol. 67,p. 2242.
    Journal of the American Chemical Society,1946,vol. 68,p. 871.
[5]Journal of the American Chemical Society,1945,vol. 67,p. 2242.
    Journal of the American Chemical Society,1946,vol. 68,p. 871.
[6]Journal of the American Chemical Society,1945,vol. 67,p. 2242.
    Journal of the American Chemical Society,1946,vol. 68,p. 871.
[7]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1977,vol. 15,p. 356 - 358.
[8]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 692 - 702.

5
[ 117-80-6 ]
[ 30709-67-2 ]
[ 64517-93-7 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1977,vol. 15,p. 356 - 358.

6
[ 30709-67-2 ]
[ 15516-47-9 ]
[ 72192-53-1 ]

References: [1]Journal of the Indian Chemical Society,1979,vol. 56,p. 521 - 524.

7
[ 30709-67-2 ]
[ 20142-88-5 ]
[ 72192-52-0 ]

References: [1]Journal of the Indian Chemical Society,1979,vol. 56,p. 521 - 524.

8
[ 30709-67-2 ]
[ 20143-41-3 ]
[ 72192-49-5 ]

References: [1]Journal of the Indian Chemical Society,1979,vol. 56,p. 521 - 524.

9
[ 30709-67-2 ]
[ 20142-87-4 ]
[ 72192-50-8 ]

References: [1]Journal of the Indian Chemical Society,1979,vol. 56,p. 521 - 524.

10
[ 30709-67-2 ]
[ 104-87-0 ]
[ 72192-66-6 ]

References: [1]Journal of the Indian Chemical Society,1979,vol. 56,p. 521 - 524.

11
[ 30709-67-2 ]
[ 99-61-6 ]
[ 62927-44-0 ]

References: [1]Journal of the Indian Chemical Society,1976,vol. 53,p. 903 - 905.

12
[ 30709-67-2 ]
[ 555-16-8 ]
[ 62878-65-3 ]

References: [1]Journal of the Indian Chemical Society,1976,vol. 53,p. 903 - 905.

13
[ 30709-67-2 ]
[ 90-02-8 ]
[ 72192-65-5 ]

References: [1]Journal of the Indian Chemical Society,1979,vol. 56,p. 521 - 524.

14
[ 30709-67-2 ]
[ 104-55-2 ]
[ 72192-67-7 ]

References: [1]Journal of the Indian Chemical Society,1979,vol. 56,p. 521 - 524.

15
[ 30709-67-2 ]
[ 701-99-5 ]
[ 72192-51-9 ]

References: [1]Journal of the Indian Chemical Society,1979,vol. 56,p. 521 - 524.

16
[ 30709-67-2 ]
[ 4122-68-3 ]
[ 72192-48-4 ]

References: [1]Journal of the Indian Chemical Society,1979,vol. 56,p. 521 - 524.

17
[ 30709-67-2 ]
[ 552-89-6 ]
[ 62878-64-2 ]

References: [1]Journal of the Indian Chemical Society,1976,vol. 53,p. 903 - 905.

18
[ 30709-67-2 ]
[ 1638-63-7 ]
[ 94547-23-6 ]

References: [1]Indian Journal of Chemistry,1963,vol. 1,p. 441 - 442.

19
[ 30709-67-2 ]
5-methyl-4-phenyl-thiazole-2-diazonium; tetrafluoroborate [ No CAS ]

References: [1]Zeitschrift fur Chemie,1970,vol. 10,p. 116.

20
(2-amino-4-phenyl-thiazol-5-ylmethyl)-triphenyl-phosphonium; chloride [ No CAS ]
[ 30709-67-2 ]

References: [1]Tetrahedron Letters,1970,p. 5107 - 5110.

21
[ 28241-61-4 ]
[ 93-55-0 ]
[ 30709-67-2 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1970,vol. 312,p. 359 - 365.

22
[ 30709-67-2 ]
[ 638-07-3 ]
[ 100003-88-1 ]

References: [1]Farmaco, Edizione Scientifica,1985,vol. 40,p. 885 - 894.

23
[ 30709-67-2 ]
[ 79-04-9 ]
[ 53968-19-7 ]

References: [1]Farmaco, Edizione Scientifica,1986,vol. 41,p. 788 - 793.
[2]Phosphorus, Sulfur and Silicon and the Related Elements,2019,vol. 194,p. 820 - 828.

24
[ 30709-67-2 ]
[ 95-92-1 ]
[ 136810-99-6 ]

References: [1]Synthesis,1991,p. 763 - 764.

25
[ 30709-67-2 ]
[ 621-30-7 ]
[ 80589-47-5 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1981,vol. 20,p. 927 - 929.

26
[ 30709-67-2 ]
[ 74-88-4 ]
3,5-dimethyl-2-imino-4-phenyl-4-thiazoline hydroiodide [ No CAS ]

References: [1]Tetrahedron,1993,vol. 49,p. 3411 - 3424.

27
[ 81171-43-9 ]
[ 17356-08-0 ]
[ 30709-67-2 ]

References: [1]Tetrahedron,1993,vol. 49,p. 3411 - 3424.

28
[ 87456-64-2 ]
[ 17356-08-0 ]
[ 30709-67-2 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1993,vol. 32,p. 364.

29
[ 2114-00-3 ]
[ 17356-08-0 ]
[ 30709-67-2 ]

Yield	Reaction Conditions	Operation in experiment
77%	In ethanol; for 1h;Reflux;	5-Methyl-4-phenylthiazol-2-amine. A mixture of 2-bromo-1-phenylpropan-1-one (3.00 g, 19.5 mmol) and thiourea (1.56 g, 20.5 mmol) in 95% EtOH (30 mL) was heated at reflux for 60 min. The solution was concentrated and mixed with water (100 mL) and saturated aqueous Na2CO3 (5.0 mL). The resultant precipitate was filtered and recrystallized in toluene. The solids were filtered and dried under vacuum to give 5-methyl-4-phenylthiazol-2-amine (4.07 g) as yellow solids in 77% yield: 1H NMR (500 MHz, DMSO-d6) δ 8.85 (s, 2H), 7.54-7.49 (m, 5H), 2.28 (s, 3H).
77%	In ethanol; for 1h;Reflux;	A mixture of 2-bromo-1-phenylpropan-1-one (3.00 g, 19.5 mmol) and thiourea (1.56 g, 20.5 mmol) in 95% EtOH (30 mL) was heated at reflux for 60 min. The solution was concentrated and mixed with water (100 mL) and saturated aqueous Na2CO3 (5.0 mL). The resultant precipitate was filtered and recrystallized in toluene. The solids were filtered and dried under vacuum to give 5-methyl-4-phenylthiazol-2-amine (4.07 g) as yellow solids in 77% yield: 1H NMR (500 MHz, DMSO-d6) δ 8.85 (s, 2 H), 7.54-7.49 (m, 5 H), 2.28 (s, 3 H).
	In ethanol; for 2h;Reflux;	General procedure: The crude 2-bromo-1-(2-chlorophenyl)ethanone (0.64 mL, 4.28 mmol) was dissolved in anhydrous ethanol (10 mL) and treated with thiourea (344 mg, 4.51 mmol). After heating at reflux for 2 h, the reaction mixture was cooled to room temperature, with a yellow precipitation. The solid obtained was filtered, washed with water and ethanol and vacuum dried to afford 4b as a yellow solid (884 mg, 98.0%).

	In ethanol;Reflux;	General procedure: Haloketones (1 eq) were conjugated with thioureas (1 eq) in anhydrous ethanol (EtOH) (1ml). Reaction was stirred at reflux from 2 to 24h until the reaction was judged complete (HPLC-MS). The mixture was then extracted with ethyl acetate (3×3ml). The organic phases were concentrated in vacuum and lyophilized. Products were verified by HPLC and MS and purified with preparative HPLC. Relevant fractions were collected and concentrated to afford the desired product in 40-95% yields, with purity of >95% as determined by HPLC-MS.
	In ethanol; at 80℃; for 2h;	General procedure: To a mixture of olefin (0.5 mmol) and tween-80 (30 mL) in water (3 mL) was added DBH (214.5 mg, 0.75 mmol) at room temperature, and the mixture was stirred under the conditions as indicated in Table 1. After cooling to room temperature and removal of solvent under reduced pressure, EtOH (3 mL), thiourea (57.1 mg, 0.75 mmol) (or 0.75 mmol of N-methylthiourea/N-phenethylthiourea) were added to the mixture, and the obtained mixture was stirred for 2 h at 80 C. The mixture was diluted with ethyl acetate (60 mL). The organic phase was washed with brine (10mL x 3) and dried over Na2SO4. After concentrated under reduced pressure, the residue was purified by preparative thin layer chromatography to afford the corresponding 2-aminothiazoles.
	In ethanol; at 20℃; for 24h;	2-Bromo-1-phenylpropanone (12.78 g, 0.06 mol) and thiourea (4.57 g, 0.06 mol) were dissolved in ethanol and mixed at room temperature for 24 h. The completion of the reaction was controlled by the TLC. The mixture was filtered and obtained the raw product.

References: [1]Tetrahedron Letters,2006,vol. 47,p. 5171 - 5172.
[2]Synthetic Communications,2009,vol. 39,p. 2895 - 2906.
[3]Patent: US2011/230486,2011,A1 .Location in patent: Page/Page column 28.
[4]Patent: WO2013/82324,2013,A1 .Location in patent: Paragraph 00344.
[5]Journal of Medicinal Chemistry,2019,vol. 62,p. 3068 - 3087.
[6]Journal of the Chemical Society. Perkin transactions I,1999,p. 2425 - 2428.
[7]Heterocycles,2008,vol. 75,p. 2825 - 2833.
[8]European Journal of Medicinal Chemistry,2012,vol. 52,p. 70 - 81.
[9]Green Chemistry,2016,vol. 18,p. 1455 - 1458.
[10]Journal of the Chinese Chemical Society,2017,vol. 64,p. 1408 - 1416.
[11]European Journal of Medicinal Chemistry,2018,vol. 144,p. 179 - 200.
[12]Tetrahedron,2018,vol. 74,p. 3602 - 3607.
[13]Phosphorus, Sulfur and Silicon and the Related Elements,2019,vol. 194,p. 820 - 828.
[14]European Journal of Organic Chemistry,2019,vol. 2019,p. 2520 - 2527.

Yield	Reaction Conditions	Operation in experiment
98%	In ethanol; for 2h;Inert atmosphere; Reflux;	General procedure: A mixture of the substrate (i.e. appropriate bromoketone) (1 eq) and thiourea (1.5 eq) in EtOH (3 mL per 1 mmol of bromoketone, unless stated otherwise) was refluxed for 2 h (unless stated otherwise).

31
[ 333-20-0 ]
[ 2114-00-3 ]
[ 30709-67-2 ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 1717 - 1720.

32
[ 30709-67-2 ]
[ 15761-38-3 ]
[1-(5-methyl-4-phenyl-thiazol-2-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 771 - 775.

33
[ 333-20-0 ]
[ 2114-00-3 ]
bis[2-(4-phenyl-5-methyl)thiazoyl] amine [ No CAS ]
[ 30709-67-2 ]

References: [1]Tetrahedron,2006,vol. 62,p. 3201 - 3213.

34
[ 30709-67-2 ]
2-amino-N-(5-methyl-4-phenyl-thiazol-2-yl)-propionamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 771 - 775.

35
[ 30709-67-2 ]
[ 105602-33-3 ]

References: [1]Farmaco, Edizione Scientifica,1986,vol. 41,p. 788 - 793.

Historical Records

Technical Information

• Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

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Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 30709-67-2

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CAS No.: 30709-67-2

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[ 30709-67-2 ] Synthesis Path-Downstream 1~35

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