6396-76-5|1-(2,6-Dimethylphenyl)thiourea| Ambeed

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Structure of 1-(2,6-Dimethylphenyl)thiourea
CAS No.: 6396-76-5

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Quality Control of [ 6396-76-5 ] Purity: 98% SDS Specification

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Product Details of [ 6396-76-5 ]

CAS No. :	6396-76-5
Formula :	C₉H₁₂N₂S
M.W :	180.27
SMILES Code :	S=C(N)NC1=C(C)C=CC=C1C
MDL No. :	MFCD00041165
InChI Key :	ASNKJUONFPQYPC-UHFFFAOYSA-N
Pubchem ID :	853911

Safety of [ 6396-76-5 ]

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

Application In Synthesis of [ 6396-76-5 ]

* 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 [ 6396-76-5 ]

[ 6396-76-5 ] Synthesis Path-Downstream 1~54

1
[ 6396-76-5 ]
[ 122239-67-2 ]

References: [1]Journal of the Chemical Society,1957,p. 4461,4467.
[2]Journal of the Chemical Society,1957,p. 4461,4467.

2
[ 6396-76-5 ]
(2,6-dimethyl-phenyl)-[4-(2,6-dimethyl-phenyl)-5-imino-4,5-dihydro-[1,2,4]thiadiazol-3-yl]-amine [ No CAS ]

References: [1]Indian Journal of Chemistry,1963,vol. 1,p. 391 - 394.

3
[ 6396-76-5 ]
[ 87-34-3 ]

References: [1]Journal of the Chemical Society,1957,p. 4461,4467.

4
[ 6544-02-1 ]
[ 87-62-7 ]
[ 6396-76-5 ]

References: [1]Organic Syntheses,1955,vol. 45,p. 70.

5
[ 1147550-11-5 ]
[ 87-62-7 ]
[ 6396-76-5 ]

References: [1]Journal of the Chemical Society,1957,p. 4461,4467.

6
[ 19241-16-8 ]
[ 6396-76-5 ]

References: [1]Journal of the Chemical Society,1927,p. 440.

7
[ 75-77-4 ]
[ 6396-76-5 ]
[ 69859-10-5 ]

References: [1]Liebigs Annalen der Chemie,1979,p. 263 - 277.

8
[ 623-46-1 ]
[ 6396-76-5 ]
[ 54708-12-2 ]

References: [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 90 - 99.

9
[ 6396-76-5 ]
3-(2,6-dimethyl-anilino)-4-(2,6-dimethyl-phenyl)-4H-[1,2,4]thiadiazol-5-ylideneamine [ No CAS ]

References: [1]Indian Journal of Chemistry,1963,vol. 1,p. 391 - 394.

10
[ 87544-32-9 ]
[ 6396-76-5 ]
[ 87544-49-8 ]

References: [1]Acta Chimica Hungarica,1983,vol. 112,p. 323 - 334.
[2]Acta Chimica Hungarica,1983,vol. 112,p. 323 - 334.

11
[ 6396-76-5 ]
[ 74-88-4 ]
[ 27806-86-6 ]

References: [1]Synthesis,1988,p. 460 - 466.

12
[ 6396-76-5 ]
[ 109-77-3 ]
[ 159615-60-8 ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 3828 - 3833.

13
[ 540-72-7 ]
[ 87-62-7 ]
[ 6396-76-5 ]

References: [1]Journal of Medicinal Chemistry,1972,vol. 15,p. 1024 - 1027.

15
[ 70-23-5 ]
[ 6396-76-5 ]
[ 736970-97-1 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 60℃;	To a round-bottomed flask were added 1-(2,6-dimethylphenyl)-2-thiourea (3.0 g, 16.6 mmol, Transworld Chemicals), ethyl bromopyruvate (2.1 mL, 16.6 mmol, Aldrich) and EtOH (40 mL). The reaction mixture was stirred at 60 C. overnight. Solvent was removed in vacuo. Purification by silica gel chromatography (gradient: 0-50% EtOAc in hexane, followed by 0-10% MeOH in CH2Cl2) provided the title compound as a white solid. MS (ESI, pos. ion) m/z: 277 (M+1).

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5211 - 5217.
[2]Patent: US2004/157845,2004,A1 .Location in patent: Page 14.

16
[ 25343-24-2 ]
[ 6396-76-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium hydroxide; at 80℃; for 0.25h;	[0335] (2,6-DIMETHYLPHENYL THIOUREA, 20. Solid N-((2,6- dimethylphenyl)carbamothioyl)benzamide (0.50 g, 1.8 mmol) was added in one portion to a 5 mL soln of 5% NaOH heated to 80C. After 15 min of vigorous stirring the mixture is poured into ice-cold 2N HC1. The pH was then adjusted to apprx. 8.5 with Na2C03 and the resulting white solid was collected by filtration, washed with H20, and dried to give 0.24 g (75%) of (2,6- dimethylphenyl)thiourea. 1H-NMR (CDC13; 300 MHz): δ 7.51 (bs, 1H), 7.24-7.19 (m, 1H), 7.16-7.14 (m, 2H), 6.04 (bs, 1H), 5.32 (bs, 1H), 2.31 (s, 6H) ppm.
	With sodium hydroxide; at 80℃;	Compound 27 Compound 28 Compound 27 (23.46g, 82.49 mmol) was suspended in 200 ml of NaOH (4N) and the mixture was stirred at 80C After the completion of reaction, the temperature was cooled down to room temperature. The Compound 28 was obtained by filtration and washing with 500 ml of H20.

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 363 - 367.
[2]Patent: WO2014/113607,2014,A1 .Location in patent: Paragraph 0335.
[3]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5211 - 5217.
[4]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 6385 - 6397.
[5]Archiv der Pharmazie,2013,vol. 346,p. 891 - 900.
[6]MedChemComm,2016,vol. 7,p. 1768 - 1774.
[7]Patent: WO2017/114742,2017,A1 .Location in patent: Page/Page column 26.
[8]MedChemComm,2018,vol. 9,p. 995 - 1010.

17
[ 6396-76-5 ]
[ 736971-00-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5211 - 5217.

18
[ 6396-76-5 ]
{2-[(2,6-dimethylphenyl)amino](1,3-thiazol-4-yl)}-N-[4-(trifluoromethyl)-phenyl]carboxamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5211 - 5217.

19
[ 87-62-7 ]
[ 6396-76-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5211 - 5217.
[2]Journal of the Chemical Society,1927,p. 440.
[3]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 6385 - 6397.
[4]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 363 - 367.
[5]Patent: WO2014/113607,2014,A1 .
[6]MedChemComm,2016,vol. 7,p. 1768 - 1774.
[7]Patent: WO2017/114742,2017,A1 .
[8]MedChemComm,2018,vol. 9,p. 995 - 1010.

20
[ 6396-76-5 ]
C₆₀H₆₂N₉O₈S₃⁽¹⁺⁾*Cl^(1-) [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 3828 - 3833.

21
[ 6396-76-5 ]
C₂₉H₃₁N₉O₇S₃ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 3828 - 3833.

22
[ 6396-76-5 ]
[ 65070-10-2 ]

References: [1]Synthesis,1988,p. 460 - 466.

23
(2,6-Dimethyl-phenylamino)-acetic acid tert-butyl ester [ No CAS ]
[ 6396-76-5 ]

References: [1]Acta Chimica Hungarica,1983,vol. 112,p. 323 - 334.

24
[ 6396-76-5 ]
N,N'-bis-(2,6-dimethyl-phenyl)-[1,2,4]thiadiazole-3,5-diamine [ No CAS ]

References: [1]Indian Journal of Chemistry,1963,vol. 1,p. 391 - 394.

25
[ 6396-76-5 ]
[3-(2,6-dimethyl-anilino)-4-(2,6-dimethyl-phenyl)-4H-[1,2,4]thiadiazol-5-ylidene]-phenyl-thiourea [ No CAS ]

References: [1]Indian Journal of Chemistry,1963,vol. 1,p. 391 - 394.

26
[ 6396-76-5 ]
[ 5349-17-7 ]
[ 1187669-29-9 ]

Yield	Reaction Conditions	Operation in experiment
91%		Example 1-82 7V-(2,6-Dimethylphenyl)-4-(4-pyridinyl)-l,3-thiazol-2-amine (137). [0347] 7V-(2,6-dimethylphenyl)-4-(4-pyridinyl)-l,3-thiazol-2-amine (137). A mixture of bromoketone hydrobromide 1 (0.30 g, 1.1 mmol) and iV-(2,6- difluorophenyl)thiourea (136) (0.20 g, 1.1 mmol) in EtOH (15 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 0 0C for 1 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 137 (0.28 g, 91%) as a white powder: mp (EtO Ac/pet, ether) 208-210 0C; 1U NMR δ 9.34 (s, 1 H, NH), 8.55 (dd, J= 4.6, 1.6 Hz, 2 H, H-2', H-6'), 7.72 (dd, J = <n="153"/>4.6, 1.6 Hz, 2 H, H-3', H-5'), 7.46 (s, 1 H, H-5), 7.12-7.19 (m, 3 H, H-3", H-4", H-5"), 2.23 (s, 6 H, 2 x CH3); 13C NMR δ 168.5, 149.9 (2), 147.9, 141.4, 137.7, 135.7 (2), 128.4 (2), 127.0, 119.8 (2), 106.1, 17.8 (2); MS m/z 282.6 (MH+, 100%). Anal, calcd for Ci6Hi5N3S: C, 68.30; H, 5.37; N, 14.93. Found: C, 68.52; H, 5.47; N, 15.14%.

References: [1]Patent: WO2009/114552,2009,A1 .Location in patent: Page/Page column 151-152.

27
[ 6396-76-5 ]
[ 96-32-2 ]
[ 1392735-23-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With sodium acetate; In ethanol; for 1h;Reflux;	Example 11: Preparation of (Z)-2-(2,6-dimethylphenylimino)-3-((£)-4-(l-(4- (trifluoromethoxy)phenyl)-lH-l,2,4-triazol-3-yl)benzylideneamino)thiazolidin-4-one (Compound 81C) (Synthesis Method I) To a solution of l-<strong>[6396-76-5](2,6-dimethylphenyl)thiourea</strong> (1.0 g, 5.55 mmol) in EtOH (10 mL) was added methyl 2-bromoacetate (1.0 g, 6.5 mmol) and sodium acetate (1.0 g, 12.2 mmol). The solution was stirred and heated to reflux for 1 h, then it was cooled and the liquid was decanted from a small amount of solid material and the liquid was then diluted with water (10 mL). The precipitate was isolated by filtration to give (1.1 g, 83%) of (Z)-3-amino-2-(2,6- dimethylphenylimino)thiazolidin-4-one: mp 149-152 C; ]H NMR (400 MHz, CDC13) δ 7.06 (d, / = 7.2 Hz, 2H), 6.98 (m, 1H), 4.75 (s, 2H), 3.80 (s, 2H), 2.12 (s, 6H); ESIMS m/z 236 (M+H).
83%	With sodium acetate; In ethanol; for 1h;Reflux;	To a solution of <strong>[6396-76-5]1-<strong>[6396-76-5](2,6-dimethylphenyl)thiourea</strong></strong> (1.0 g, 5.55 mmol) in EtOH (10 mL) was added methyl 2-bromoacetate (1.0 g, 6.5 mmol) and sodium acetate (1.0 g, 12.2 mmol). The solution was stirred and heated to reflux for 1 h, then it was cooled and the liquid was decanted from a small amount of solid material and the liquid was then diluted with water (10 mL). The precipitate was isolated by filtration to give (1.1 g, 83%) of (Z)-3-amino-2-(2,6-dimethylphenylimino)thiazolidin-4-one: mp 149-152 C.; 1H NMR (400 MHz, CDCl3) δ 7.06 (d, J=7.2 Hz, 2H), 6.98 (m, 1H), 4.75 (s, 2H), 3.80 (s, 2H), 2.12 (s, 6H); ESIMS m/z 236 (M+H).
83%	With sodium acetate; In ethanol; for 1h;Reflux;	To a solution of <strong>[6396-76-5]1-<strong>[6396-76-5](2,6-dimethylphenyl)thiourea</strong></strong> (1.0 g, 5.55 mmol) in EtOH (10 mL) was added methyl 2-bromoacetate (1.0 g, 6.5 mmol) and sodium acetate (1.0 g, 12.2 mmol). The solution was stirred and heated to reflux for 1 h, then it was cooled and the liquid was decanted from a small amount of solid material and the liquid was then diluted with water (10 mL). The precipitate was isolated by filtration to give (1.1 g, 83%) of (Z)-3-amino-2-(2,6-dimethylphenylimino)thiazolidin-4-one: mp 149-152 C.; 1H NMR (400 MHz, CDCl3) δ 7.06 (d, J=7.2 Hz, 2H), 6.98 (m, 1H), 4.75 (s, 2H), 3.80 (s, 2H), 2.12 (s, 6H); ESIMS m/z 236 (M+H).

83%

With sodium acetate; In ethanol; for 1h;Reflux;

Example 11 Preparation of (Z)-2-(2,6-dimethylphenylimino)-3-((E)-4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylideneamino)thiazolidin-4-one (Compound 81C) (Synthesis Method I) To a solution of [6396-76-5]1-[6396-76-5](2,6-dimethylphenyl)thiourea (1.0 g, 5.55 mmol) in EtOH (10 mL) was added methyl 2-bromoacetate (1.0 g, 6.5 mmol) and sodium acetate (1.0 g, 12.2 mmol). The solution was stirred and heated to reflux for 1 h, then it was cooled and the liquid was decanted from a small amount of solid material and the liquid was then diluted with water (10 mL). The precipitate was isolated by filtration to give (1.1 g, 83%) of (Z)-3-amino-2-(2,6-dimethylphenylimino)thiazolidin-4-one: mp 149-152 C.; 1H NMR (400 MHz, CDCl3) δ 7.06 (d, J=7.2 Hz, 2H), 6.98 (m, 1H), 4.75 (s, 2H), 3.80 (s, 2H), 2.12 (s, 6H); ESIMS m/z 236 (M+H).

References: [1]Patent: WO2012/109125,2012,A1 .Location in patent: Page/Page column 26.
[2]Patent: US2013/203592,2013,A1 .Location in patent: Paragraph 0125; 0126.
[3]Patent: US2013/203593,2013,A1 .Location in patent: Paragraph 0124; 0125.
[4]Patent: US2016/135464,2016,A1 .Location in patent: Paragraph 0125; 0126.

28
[ 6396-76-5 ]
[ 1392724-38-7 ]

References: [1]Patent: WO2012/109125,2012,A1 .

29
[ 6396-76-5 ]
[ 96-32-2 ]
[ 1392735-23-7 ]
[ 1392724-38-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; In ethanol;	Example 11 Preparation of (Z)-2-(2,6-dimethylphenylimino)-3-((E)-4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylideneamino)thiazolidin-4-one (Compound 81C) (Synthesis Method I) To a solution of <strong>[6396-76-5]1-<strong>[6396-76-5](2,6-dimethylphenyl)thiourea</strong></strong> (1.0 g, 5.55 mmol) in EtOH (10 mL) was added methyl 2-bromoacetate (1.0 g, 6.5 mmol) and sodium acetate (1.0 g, 12.2 mmol). The solution was stirred and heated to reflux for 1 h, then it was cooled and the liquid was decanted from a small amount of solid material and the liquid was then diluted with water (10 mL). The precipitate was isolated by filtration to give (1.1 g, 83%) of (Z)-3-amino-2-(2,6-dimethylphenylimino)thiazolidin-4-one: mp 149-152 C.; 1H NMR (400 MHz, CDCl3) δ 7.06 (d, J=7.2 Hz, 2H), 6.98 (m, 1H), 4.75 (s, 2H), 3.80 (s, 2H), 2.12 (s, 6H); ESIMS m/z 236 (M+H).

References: [1]Patent: US2012/202687,2012,A1 .Location in patent: Page/Page column.

30
[ 6396-76-5 ]
[ 17570-98-8 ]
N-(2,6-dimethylphenyl)-4-(2-pyridinyl)-1,3-thiazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%		General procedure: 5.1.1 General procedure A (for synthesis of compounds 1-19). To 2-bromoacetylpyridine hydrobromide (1.0 equiv) in anhydrous ethanol (5 mL) was added the corresponding thiourea (1.0 equiv, 0.2 g) and the reaction mixture refluxed for 4 h. After cooling to ambient temperature the reaction mixture was poured into water. The pH of the mixture was adjusted to pH 8 with concentrated aqueous NH4OH and the mixture stirred for 2 h. The precipitate was filtered, washed with ethanol and dried to afford the title compound.
57%	In ethanol; at 70℃; for 2h;	General procedure: Compounds 17-29and 43-61 were prepared following this general protocol unless otherwise noted. To substituted2-bromoethanone in ethanol was added substituted thiourea (1.02 eq). The mixture wasstirred at 70C. The reaction was monitored via LC/MS. After 2 h, the reaction mixture wascooled to room temperature and precipitate was formed. The precipitate was collected by vacuumfiltration and washed with acetone. The solid was dissolved in 2 MNaOH (25 mL) and extracted with EtOAc (3 x 50 mL). The combined organic layers were dried over Na2SO4 andconcentrated in vacuo desired product.

References: [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 6385 - 6397.
[2]PLoS ONE,2016,vol. 11.

31
[ 5308-51-0 ]
[ 6396-76-5 ]
1-[2-(2,6-dimethylanilino)thiazol-4-yl]ethanone [ No CAS ]

References: [1]MedChemComm,2013,vol. 4,p. 1513 - 1522.

32
3-methyl-4-(2,2,2-trifluoroethoxy)-2-chloromethylpyridine hydrochloride [ No CAS ]
[ 6396-76-5 ]
N-(2,6-dimethylphenyl)-S-2-(3-methyl-4-(2',2',2'-trifluoroethoxy)pyridylmethyl)isothiourea dihydrochloride [ No CAS ]

References: [1]Archiv der Pharmazie,2013,vol. 346,p. 891 - 900.

33
[ 6396-76-5 ]
[ 1215796-41-0 ]
N-(2,6-dimethylphenyl)-S-2-(4-ethoxypyridylmethyl)isothiourea dihydrochloride [ No CAS ]

References: [1]Archiv der Pharmazie,2013,vol. 346,p. 891 - 900.

34
[ 6396-76-5 ]
[ 74-88-4 ]
[ 52789-85-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	In ethanol; for 1h;Reflux;	[0336] METHYL N,-(2,6-DIMETHYLPHENYL CARBAMIMIDOTHIOATE, 21. (2,6- dimethylphenyl)thiourea (0.81 g, 4.5 mmol, 1 eq) was mixed with methyl iodide (0.77 g, 5.4 mmol, 1.2 eq) and refluxed in EtOH for 1 h. Reaction mixture was concentrated under reduced pressure, diluted with Na2C03 soln and extract into Et20 which was dried and removed give 0.89 g of methyl ^-( ^-dimethylpheny^carbamimidothioate (85%) as a yellow solid. 1H-NMR (CDC13; 400 MHz): δ 7.02 (d, J= 7.4 Hz, 2H), 6.87 (t, J= 7.4 Hz, 1H), 4.27 (bs, 2H), 2.53 (bs, 3H), 2.1 1 (s, 6H) ppm.

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 363 - 367.
[2]Patent: WO2014/113607,2014,A1 .Location in patent: Paragraph 0336; 0357.

35
[ 6396-76-5 ]
[ 124111-95-1 ]

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 363 - 367.
[2]Patent: WO2014/113607,2014,A1 .

36
[ 6396-76-5 ]
2-(4-bromobenzylidene)-N'-(2,6-dimethylphenyl)hydrazinecarboximidamide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 363 - 367.
[2]Patent: WO2014/113607,2014,A1 .

37
[ 6160-65-2 ]
[ 87-62-7 ]
[ 6396-76-5 ]

References: [1]Chemical Science,2016,vol. 7,p. 2322 - 2330.

38
[ 6396-76-5 ]
[ 70-11-1 ]
N-(2,6-dimethylphenyl)-4-phenyl-1,3-thiazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In ethanol; at 70℃; for 2h;	General procedure: Compounds 17-29and 43-61 were prepared following this general protocol unless otherwise noted. To substituted2-bromoethanone in ethanol was added substituted thiourea (1.02 eq). The mixture wasstirred at 70C. The reaction was monitored via LC/MS. After 2 h, the reaction mixture wascooled to room temperature and precipitate was formed. The precipitate was collected by vacuumfiltration and washed with acetone. The solid was dissolved in 2 MNaOH (25 mL) and extracted with EtOAc (3 x 50 mL). The combined organic layers were dried over Na2SO4 andconcentrated in vacuo desired product.

References: [1]PLoS ONE,2016,vol. 11.
[2]European Journal of Organic Chemistry,2021,vol. 2021,p. 3587 - 3597.

39
[ 10531-41-6 ]
[ 6396-76-5 ]
N-(2,6-dimethylphenyl)-4-(thiophen-2-yl)-1,3-thiazol-2-amine [ No CAS ]