[ CAS No. 3096-71-7 ] {[proInfo.proName]}

Name: 3096-71-7|4-Amino-2,5-dimethylphenol|97%
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SKU: A100740
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Quality Control of [ 3096-71-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 3096-71-7 ]

CAS No. :	3096-71-7	MDL No. :	MFCD00007873
Formula :	C₈H₁₁NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JSWVCUXQICMATE-UHFFFAOYSA-N
M.W :	137.18	Pubchem ID :	76544
Synonyms :

Calculated chemistry of [ 3096-71-7 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	42.8
TPSA :	46.25 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.49
Log Po/w (XLOGP3) :	1.61
Log Po/w (WLOGP) :	1.6
Log Po/w (MLOGP) :	1.48
Log Po/w (SILICOS-IT) :	1.55
Consensus Log Po/w :	1.55

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.15
Solubility :	0.974 mg/ml ; 0.0071 mol/l
Class :	Soluble
Log S (Ali) :	-2.19
Solubility :	0.879 mg/ml ; 0.00641 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.21
Solubility :	0.85 mg/ml ; 0.00619 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 3096-71-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3096-71-7 ]

* 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.

Upstream synthesis route of [ 3096-71-7 ]
Downstream synthetic route of [ 3096-71-7 ]

[ 3096-71-7 ] Synthesis Path-Upstream 1~15

1
[ 3096-64-8 ]
[ 20782-94-9 ]
[ 3096-71-7 ]

Reference： [1] Canadian Journal of Chemistry, 1996, vol. 74, # 7, p. 1321 - 1328

2
[ 2593-53-5 ]
[ 3096-71-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With hydrogenchloride; tin(ll) chloride In dichloromethane; water for 16 h; Reflux	General procedure: A mixture of the para-benzoquinone mono-oxime (1.26 mmol),SnCl2 (0.72 g, 3.80 mmol), 20 mL of CH2Cl2, and 0.2 mL of concentrated HCl, was heated to reflux for 16 h. The CH2Cl2 was removed under reduced pressure, and the residue was dissolved in ethyl acetate and washed with concentrated aqueous NaHCO3. The organic layer was dried over anhydrous Na2SO4 and the filtrate was concentrated under reduced pressure to afford the solid product.

Reference： [1] Tetrahedron, 2014, vol. 70, # 39, p. 6963 - 6973
[2] Chemische Berichte, 1885, vol. 18, p. 570
[3] Chemische Berichte, 1887, vol. 20, p. 979
[4] Journal of the American Chemical Society, 1917, vol. 39, p. 2190
[5] Journal of the American Chemical Society, 2016, vol. 138, # 16, p. 5202 - 5205

3
[ 95-87-4 ]
[ 3096-71-7 ]

Reference： [1] Journal of Organic Chemistry, 1941, vol. 6, p. 427,431
[2] Gazzetta Chimica Italiana, 1963, vol. 93, p. 1056 - 1065
[3] Tetrahedron, 2014, vol. 70, # 39, p. 6963 - 6973
[4] Tetrahedron, 2014, vol. 70, # 39, p. 6963 - 6973
[5] Journal of the American Chemical Society, 2016, vol. 138, # 16, p. 5202 - 5205
[6] Patent: WO2017/83719, 2017, A1, . Location in patent: Page/Page column 74; 75

4
[ 89-58-7 ]
[ 3096-71-7 ]

Reference： [1] Chemische Berichte, 1894, vol. 27, p. 1930
[2] Bulletin de la Societe Chimique de France, 1966, p. 1848 - 1858

5
[ 3139-05-7 ]
[ 3096-71-7 ]

Reference： [1] Gazzetta Chimica Italiana, 1963, vol. 93, p. 1056 - 1065

6
[ 19499-98-0 ]
[ 3096-71-7 ]

Reference： [1] Gazzetta Chimica Italiana, 1963, vol. 93, p. 1056 - 1065

7
[ 835-84-7 ]
[ 3096-71-7 ]

Reference： [1] Gazzetta Chimica Italiana, 1963, vol. 93, p. 1056 - 1065

8
[ 137-18-8 ]
[ 3096-71-7 ]

Reference： [1] Chemische Berichte, 1885, vol. 18, p. 570
[2] Chemische Berichte, 1887, vol. 20, p. 979
[3] Tetrahedron, 2014, vol. 70, # 39, p. 6963 - 6973

9
[ 3096-64-8 ]
[ 3096-71-7 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1981, p. 1596 - 1598
[2] Justus Liebigs Annalen der Chemie, 1921, vol. 424, p. 300[3] Justus Liebigs Annalen der Chemie, 1925, vol. 441, p. 303
[4] Dissert.<Zuerich 1899>,S.32,

10
[ 95-68-1 ]
[ 3096-71-7 ]

Reference： [1] Helvetica Chimica Acta, 1925, vol. 8, p. 297

11
[ 3096-64-8 ]
[ 20782-94-9 ]
[ 3096-71-7 ]

Reference： [1] Canadian Journal of Chemistry, 1996, vol. 74, # 7, p. 1321 - 1328

12
[ 7664-93-9 ]
[ 95-68-1 ]
[ 3096-71-7 ]

Reference： [1] Helvetica Chimica Acta, 1925, vol. 8, p. 297

13
[ 7664-93-9 ]
[ 3096-64-8 ]
[ 615-90-7 ]
[ 3096-71-7 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1921, vol. 424, p. 300[2] Justus Liebigs Annalen der Chemie, 1925, vol. 441, p. 303
[3] Diss. <Zuerich 1899>, S. 30,

14
[ 7647-01-0 ]
[ 3096-71-7 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1926, vol. 447, p. 180

15
[ 64-17-5 ]
[ 35774-21-1 ]
[ 7664-93-9 ]
[ 615-90-7 ]
[ 3096-71-7 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1925, vol. 443, p. 205
[2] Dissert. <Zuerich 1902>, S. 52,

[ 3096-71-7 ] Synthesis Path-Downstream 1~88

1
[ 3096-71-7 ]
[ 150-86-7 ]
(2RS)-2,5,8-Trimethyl-6-(-4-nitro-benzoylamino)-2-((4R,8R)-4,8,12-trimethyl-tridecyl)-chroman [ No CAS ]

Reference： [1]Patent: DE706795,1939,
DRP/DRBP Org.Chem.,
[2]Patent: US2358287,1941,

2
[ 89-58-7 ]
[ 3096-71-7 ]

Reference： [1]Chemische Berichte,1894,vol. 27,p. 1930
[2]Bulletin de la Societe Chimique de France,1966,p. 1848 - 1858

3
[ 2832-19-1 ]
[ 3096-71-7 ]
N-(3-Amino-6-hydroxy-2,5-dimethyl-benzyl)-2-chloro-acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 1414 - 1427

4
[ 3139-05-7 ]
[ 3096-71-7 ]

Reference： [1]Gazzetta Chimica Italiana,1963,vol. 93,p. 1056 - 1065

5
[ 1121-60-4 ]
[ 3096-71-7 ]
2,5-Dimethyl-4-[1-pyridin-2-yl-meth-(E)-ylidene]-amino}-phenol [ No CAS ]

Reference： [1]Chemical Communications,2005,p. 5217 - 5219

6
[ 3096-71-7 ]
[ 53839-60-4 ]
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid (4-hydroxy-2,5-dimethyl-phenyl)-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 836 - 840

7
[ 3096-71-7 ]
(2,5-Dimethyl-4-trimethylsilanyloxy-phenyl)-[1-pyridin-2-yl-meth-(E)-ylidene]-amine [ No CAS ]

Reference： [1]Chemical Communications,2005,p. 5217 - 5219

8
[ 3096-71-7 ]
C₇₆H₁₀₀N₈O₄Si₅ [ No CAS ]

Reference： [1]Chemical Communications,2005,p. 5217 - 5219

9
[ 3096-71-7 ]
aqueous iron chloride [ No CAS ]
2-ethyl-4-methoxy-6-methyl-1H-indole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 5119 - 5136

10
[ 3096-71-7 ]
aqueous iron chloride [ No CAS ]
[ 185063-85-8 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 5119 - 5136

11
[ 3096-71-7 ]
aqueous iron chloride [ No CAS ]
1-Benzyl-2-ethyl-4-methoxy-6-methyl-1H-indole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 5119 - 5136

12
[ 3096-71-7 ]
aqueous iron chloride [ No CAS ]
1-(tert-butoxycarbonyl)-2-ethyl-5-methoxy-6-methyl-1H-indole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 5119 - 5136

13
[ 3096-71-7 ]
aqueous iron chloride [ No CAS ]
[ 185063-87-0 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 5119 - 5136

14
[ 3096-71-7 ]
[ 75552-07-7 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 1414 - 1427

15
[ 137-18-8 ]
[ 3096-71-7 ]

Reference： [1]Chemische Berichte,1885,vol. 18,p. 570
[2]Tetrahedron,2014,vol. 70,p. 6963 - 6973

16
[ 3096-71-7 ]
acetic acid-(5,8-dimethyl-[6]quinolyl ester) [ No CAS ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1940,vol. 60,p. 271,278; dtsch. Ref. S. 98, 103
Chem.Abstr.,1941,p. 458

17
[ 3096-71-7 ]
[ 861796-92-1 ]

Reference： [1]Journal of the American Chemical Society,1917,vol. 39,p. 2190

18
[ 3096-71-7 ]
(4-amino-2,5-dimethyl-phenoxy)-acetic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1917,vol. 39,p. 2190

19
[ 3096-71-7 ]
(4-amino-2,5-dimethyl-phenoxy)-acetic acid ethyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1917,vol. 39,p. 2190

20
[ 3096-71-7 ]
[ 861296-03-9 ]

Reference： [1]Journal of the American Chemical Society,1917,vol. 39,p. 2190

21
[ 835-84-7 ]
[ 3096-71-7 ]

Reference： [1]Gazzetta Chimica Italiana,1963,vol. 93,p. 1056 - 1065

22
[ 3096-71-7 ]
[ 108-24-7 ]
[ 3096-93-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With pyridine; In ethyl acetate; for 1h;Heating / reflux;	Acetic anhydride (0.894 ml, 9.48 mmol) and pyridine (1 ml) were added to a solution of 2,5-dimethy-4-aminophenol (500 mg, 3.64 mmol) in ethyl acetate (5 ml), and the resulting mixture was refluxed. After 1 hour, hexane (50 ml) was poured into the reaction solution and the crystals formed were filtered under reduced pressure and then dried to obtain 4-(acetylamino)-2,5-dimethylphenyl acetate (763 mg, 95%).
	With potassium acetate; In chloroform; at 20℃;Heating / reflux;	EXAMPLE 105; 2-(l-(4-Fluorophenyl)-lH-indazol-5-yl)-N-(thiazol-2- yl)cyclopropanecarboxamide; (a) Following the general procedure of Sun et al (J. Org. Chem. 1997, 62,5627-5629), 4-amino-2-methyl-5-methylphenol (10 g, 72.9 mmol) was dissolved in dry chloroform (150 mL) followed by potassium acetate (14.3 g, 146 mmol), and acetic anhydride (22 g, 219 mmol). After 2 h, the reaction was refluxed for 3 h and then cooled to rt and stirred overnight.

Reference： [1]Patent: EP1403255,2004,A1 .Location in patent: Page 109
[2]Patent: WO2008/57856,2008,A2 .Location in patent: Page/Page column 112

23
[ 101494-82-0 ]
[ 3096-71-7 ]
2,5-dimethyl-4-[(3-phenyl-1,2,4-thiadiazol-5-yl)oxy]phenylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide; ice-water; mineral oil;	Preparation of 2,5-dimethyl-4-[(3-phenyl-1,2,4-thiadiazol-5-yl)oxy]phenylamine 4-Amino-2,5-dimethylphenol (10.5 g) is added at room temperature to a suspension of sodium hydride (60% dispersion in mineral oil, 3 g) in anhydrous dimethylformamide (300 ml). The reaction mixture is stirred for 30 minutes and 5-bromo-3-phenyl-1,2,4-thiadiazole (18 g) prepared according to Chem. Ber. 1961, 94, 2043 is then added slowly. After stirring for 15 h, the reaction mixture is diluted in ice-water and then extracted with diethyl ether. Drying over magnesium sulphate followed by concentration of the combined organic phases gives the title compound.

Reference： [1]Patent: US2003/8884,2003,A1

24
[ 438249-84-4 ]
[ 3096-71-7 ]
4-(2,5-Dimethyl-4-hydroxyanilino)-2-(2-pyridinyl)-6-(trifluoromethyl)pyrimidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%		EXAMPLE 147 4-(2,5-Dimethyl-4-hydroxyanilino)-2-(2-pyridinyl)-6-(trifluoromethyl)pyrimidine hydrochloride The title compound was prepared from a mixture of 4-chloro-2-(2-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol) and 4-amino -2,5-dimethylphenol (40 mg, 0.290 mmol) similar to Example 117 and isolated as an orange solid (35 mg, 47%). 1H NMR (CDCl3): 8.79-8.77 (m, 1H), 8.58 (d, J=7.8 Hz, 1H), 8.14 (bs, 1H), 7.91-7.86 (m, 1H), 7.46-7.42 (m, 1H), 7.09 (bs, 1H), 6.92 (s, 1H), 6.83 (s, 1H), 6.46 (s, 1H), 2.22 (s, 3H), 2.02 (s, 3H).

Reference： [1]Patent: US2003/69239,2003,A1

25
[ 204394-69-4 ]
[ 3096-71-7 ]
[ 438249-37-7 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 201 4-(2,5-Dimethyl-4-hydroxyanilino)-2-(3-pyridinyl)-6-trifluoromethylpyrimidine The title compound was prepared from 4-chloro-2-(3-pyridinyl)-6-trifluoromethylpyrimidine (50 mg, 0.192 mmol) and 2,5-dimethyl-4-hydroxyaniline (40 mg, 0.288 mmol) similar to Example 190 and was isolated as a solid. 1H NMR (CDCl3): 9.51 (brs, 1H), 8.72 (d, J=8.4 Hz, 1H), 8.63 (d, J=3.6 Hz, 1H), 7.45 (dd, J=7.5, 3.5 Hz, 1H), 7.33 (s, 1H), 7.00 (s, 1H), 6.74 (s, 1H), 6.45 (brs, 1H), 2.25 (s, 3H), 2.16 (s, 3H).

Reference： [1]Patent: US2003/69239,2003,A1

26
[ 204394-70-7 ]
[ 3096-71-7 ]
[ 438248-85-2 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 149 4-(2,5-Dimethyl-4-hydroxyanilino)-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidine The title compound was prepared from a mixture of 4-chloro-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol) and 4-amino -2,5-dimethylphenol (40 mg, 0.290 mmol) similar to Example 117 and isolated as a white solid (2 mg). 1H NMR (CDCl3): 8.77 (d, J=6.0 Hz, 2H), 8.27 (d, J=6.3 Hz, 2H), 7.05 (s, 1H), 6.86 (s, 1H), 6.77 (s, 1H), 6.47 (s, 1H), 5.25 (bs, 1H), 2.26 (s, 3H), 2.19 (s, 3H).

Reference： [1]Patent: US2003/69239,2003,A1

27
[ 438249-85-5 ]
[ 3096-71-7 ]
4-(2,5-Dimethyl-4-hydroxyanilino)-(2-pyrazinyl)-6-(trifluoromethyl)pyrimidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%		EXAMPLE 148 4-(2,5-Dimethyl-4-hydroxyanilino)-(2-pyrazinyl)-6-(trifluoromethyl)pyrimidine hydrochloride The title compound was prepared from a mixture of 4-chloro-(2-pyrazinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.191 mmol) and <strong>[3096-71-7]4-amino-2,5-dimethylphenol</strong> (39 mg, 0.287 mmol) similar to Example 117 and isolated as an orange solid (35 mg, 47%). 1H NMR (CDCl3): 9.75 (d, J=1.2 Hz, 1H), 8.79-8.78 (m, 1H), 8.73 (d, J=2.4 Hz, 1H), 7.20 (s, 1H), 7.01 (s, 1H), 6.78 (s, 1H), 6.52 (s, 1H), 5.43 (s, 1H), 2.25 (s, 3H), 2.16 (s, 3H).

Reference： [1]Patent: US2003/69239,2003,A1

28
[ 141-86-6 ]
[ 3096-71-7 ]
aza indoaniline [ No CAS ]
[ 35940-81-9 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium persulfate; In water;	EXAMPLE 6 Preparation of N-[(2',4' diamino-3'-aza) phenyl-] 2,5-dimethyl benzoquinone imine having the formula: SPC5 Initially, 0.02 mole (2.74 g) of <strong>[3096-71-7]2,5-dimethyl-4-amino phenol</strong> is dissolved in 50 cc of 4 N soda solution. Then, 0.02 mole (2.18 g) of 2,6-diamino pyridine is dissolved in 50 cc of water. The two solutions thus prepared are mixed. The mixture is cooled to 0C and 0.02 mole (4.56 g) of ammonium persulfate in solution in 50 cc of water is added. The reaction mixture is left for an hour at 0. The desired azaindoaniline precipitates and the resulting precipitate is filtered. After washing the precipitate with water and drying the same under a vacuum, it is chromatographically pure and melts at 238.

Reference： [1]Patent: US3956342,1976,A

29
[ 35654-56-9 ]
[ 3096-71-7 ]
[ 286371-46-8 ]

Yield	Reaction Conditions	Operation in experiment
	With dimethyl sulfoxide; In water;	Production Example 3: 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,5-dimethylaniline Sodium hydride (60 wt%, 0.36 g) was added to dimethyl sulfoxide (10 ml), and the mixture was stirred at 50C for 30 min and was then cooled to room temperature. 4-Amino-2,5-dimethylphenol (1.23 g) was added to the cooled mixture, and the mixture was stirred at room temperature for 10 min. Next, 4-chloro-6,7-dimethoxyquinoline (1.00 g) was added thereto, and the mixture was stirred at 100C overnight. Water was added to the reaction solution, followed by extraction with chloroform. The chloroform layer was then washed with a saturated aqueous sodium hydrogencarbonate solution and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by chromatography on silica gel by development with chloroform/acetone (1/1) to give the title compound.

Reference： [1]Patent: EP1153920,2001,A1

30
[ 286371-49-1 ]
[ 3096-71-7 ]
[ 286371-50-4 ]

Yield	Reaction Conditions	Operation in experiment
52%	With dimethyl sulfoxide; In methanol; water;	Production Example 9: 4-[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2,5-dimethylaniline Sodium hydride (60 wt%, 1.17 g) was added to dimethyl sulfoxide (25 ml), and the mixture was stirred at 60C for 30 min and was then cooled to room temperature. Next, <strong>[3096-71-7]4-amino-2,5-dimethylphenol</strong> (4.00 g) was added thereto, and the mixture was stirred at room temperature for 10 min. 7-(Benzyloxy)-4-chloro-6-methoxyquinoline (4.36 g) was then added thereto. The mixture was stirred for 22 hr before water was added to the reaction solution, followed by extraction with chloroform. The chloroform layer was then washed with a saturated aqueous sodium hydrogencarbonate solution and was dried over anhydrous sodium sulfate. The solvent-wasremoved by distillation under the reduced pressure, and methanol was added to the residue to prepare a suspension. The precipitated crystal was collected by suction filtration to give 3.04 g (yield 52%) of the title compound. 1H-NMR (CDCl3, 400 MHz): delta 2.05 (s, 3H), 2.16 (s, 3H), 3.58 (s, 2H), 4.06 (s, 3H), 5.32 (s, 2H), 6.28 (d, J = 5.1 Hz, 1H), 6.61 (s, 1H), 6.81 (s, 1H), 7.28 - 7.42 (m, 3H), 7.44 (s, 1H), 7.49 - 7.54 (m, 2H), 7.63 (s, 1H), 8.39 (d, J = 5.1 Hz, 1H) Mass analysis, found (ESI-MS, m/z): 401 (M++1)

Reference： [1]Patent: EP1153920,2001,A1

31
[ 3934-20-1 ]
[ 3096-71-7 ]
[ 929640-96-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In water; acetone; at 20℃; for 20h;	A solution of 7.55 g (55 mmol) <strong>[3096-71-7]4-amino-2,5-dimethylphenol</strong> and 2.4 g NaOH (2M) in 30 ml water were added dropwise to a solution of 7.45 g (50.0 mmol) of 2,4-dichloropyrimidine in 50 ml of acetone. The reaction mixture was stirred for 20 h at ambient temperature. After concentration in vacuo and addition of 150 ml water the formed precipitate was filtered by suction. Yield 10.6 g (75%) with a purity of 88 % log P (pH = 2.3) = 1.37.

Reference： [1]Patent: WO2007/31524,2007,A1 .Location in patent: Page/Page column 20

32
[ 3096-71-7 ]
[ 186767-23-7 ]
4-(2-ethyl-3-chloropyridyl-4-oxy)-2,5-xylidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With potassium carbonate; In dimethyl sulfoxide; at 120℃; for 6h;	Preparation of starting material: 4-(2-Ethyl-3-chloropyridyl-4-oxy)-2,5-xylidine - compound of formula (VII); 3.11 g (22.72 mmol) of <strong>[3096-71-7]4-amino-2,5-dimethylphenol</strong>, 4.00 g (22.72 mmol) of 3,4-dichloro-2- ethylpyridine and 5.02 g (36.05 mmol) of potassium carbonate were suspended in 50 ml of DMSO under argon atmosphere. The reaction mixture was stirred at 12O0C for 6h, cooled down to room temperature, treated with 150 ml of water and 50 ml of a 2N solution of sodium hydroxide in water and extracted with dichloromethane (2x 100 ml). The combined organic extracts were dried (MgSO4), filtered and evaporated to dryness. The crude product EPO <DP n="24"/>was purified by silica gel chromatography eluting with cyclohexane/ethyl acetate to yield the title compound in 59% yield (3.7 g, 97% purity); log P (pH 2.3) = 1.66. 1H NMR delta(ppm) 1.25 (t, 3JHH = 7 Hz, 3H, CH3), 1.92 (s, 3H, CH3), 2.03 (s, 3H, CH3), 2.91 (q, 3JHH = 7 Hz, 2H, CH2), 4.64 (s, 2H, NH2), 6.37 (m, 1 H, pyridine-H), 6.57 (s, 1 H, Ph-H), 6.68 (s, 1 H, Ph-H), 8.17 (m, 1 H, pyridine-H).

Reference： [1]Patent: WO2007/31523,2007,A1 .Location in patent: Page/Page column 22-23

33
[ 5424-21-5 ]
[ 3096-71-7 ]
4-[(2-chloro-6-methylpyrimidin-4-yl)oxy]-2,5-dimethyl-aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In water; acetone; at 20℃; for 20h;	A solution of 4.53 g (33 mmol) <strong>[3096-71-7]4-amino-2,5-dimethylphenol</strong> and 1.44 g NaOH (2M) in 30 ml water were added dropwise to a solution of 4.89 g (30.0 mmol) of 2,4-dichloropyrimidine in 50 ml of acetone. The reaction mixture was stirred for 20 h at ambient temperature. After concentration in vacuo and addition of 250 ml water the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated in vacuo yielded 5.1O g (52%) with a purity of 81 %; log P (pH = 2.3) = 1.62.

Reference： [1]Patent: WO2007/31524,2007,A1 .Location in patent: Page/Page column 21-22

34
[ 3096-71-7 ]
[ 1379347-34-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In N,N-dimethyl-formamide;	1.3 g (33 mmol) sodium hydride (60% in oil) were added portionwise to a solution of 4.1 g (30.0 mmol) of <strong>[3096-71-7]4-amino-2,5-dimethylphenol</strong> in 30 ml of dimethylformamide. After the gas evolution has stopped, 5.6 g (30 mmol) of 2,4,5-trichloro-1 ,3-thiazole were added and the reaction mixture was stirred for 1 h at 100 0C. At ambient temperature 0.5 ml methanol, 10 ml of water and 100 ml of ethyl acetate were added successively. The organic layer was separated, the watery layer extracted with ethyl acetate and the combined organic layers were dreid over magnesium sulfate. Concentration in vacuo and colum chromatographie (petroleum ether / acetone 4/1 ) yielded 4.8 g (16.6 mmol, 55 %) of 4-[(4,5-dichloro-1 ,3-thiazol-2-yl)oxy]-2,5- dimethylaniline log P (pH = 2.3) = 3.4

Reference： [1]Patent: WO2007/31513,2007,A1 .Location in patent: Page/Page column 34

35
[ 3096-71-7 ]
[ 39890-98-7 ]
4-(2-chlor-4-trifluormethylpyridyl-6-oxy)-2,5-xylidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium carbonate; In dimethyl sulfoxide; at 120℃; for 6h;	Preparation of starting material: 4-(2-chlor-4-trifluormethylpyridyl-6-oxy)-2,5-xylidine - compound of formula (VII); 1.76 g (12.86 mmol) of 4-amino-2,5-dimethylphenol, 2.50 g (11.56 mmol) of 2,6-dichloro-4- trifluoromethylpyridine and 1.95 g (14.14 mmol) of potassium carbonate were suspended in 50 ml of DMSO under argon atmosphere. The reaction mixture was stirred at 12O0C for 6h, cooled down to room temperature, treated with 150 ml of water and 50 ml of a 2N solution of sodium hydroxide in water and extracted with dichloromethane (2x 100 ml). The combined organic extracts were dried (MgSO4), filtered and evaporated to dryness. The crude product was purified by silica gel chromatography eluting with cyclohexane/ethyl acetate to yield the title compound in 64% yield (2.6 g, 92% purity); log P (pH 2.3) = 2.77. 1H NMR delta(ppm) 1.92 (s, 3H, CH3), 2.02 (s, 3H, CH3), 4.73 (s, 2H, NH2), 6.52 (s, 1 H, aryl-H), 6.70 (s, 1 H, aryl-H), 7.20 (s, 1 H, aryl-H), 7.58 (s, 1 H, aryl-H).

Reference： [1]Patent: WO2007/31523,2007,A1 .Location in patent: Page/Page column 18

36
[ 771464-30-3 ]
[ 3096-71-7 ]
[ 417723-80-9 ]

Yield	Reaction Conditions	Operation in experiment
	In water; dimethyl sulfoxide; ethyl acetate;	Production Example 491-1 4-(6-Carbamoyl-7-methoxy-4-quinolyl)oxy-2,5-dimethylphenylamine 4-Amino-2,5-dimethylphenol (1.0 g) was dissolved in dimethylsulfoxide (5 ml), and then 60% sodium hydride (1.0 g) was added and the mixture was stirred for a while. After adding 7-methoxy-4-chloroquinoline-6-carboxyamide (900 mg), the mixture was heated at 100 C. for 6 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate, and then the organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was washed with ethyl acetate to obtain the title compound (135 mg). 1H-NMR (DMSO-d6) delta (ppm) 1.91 (3H, s), 2.03 (3H, s), 4.01 (3H, s), 6.26 (1H, d, J=5.2 Hz), 6.57 (1H, s), 6.77 (1H, s), 7.46 (1H, s), 7.70 (1H, brs), 7.83 (1H, brs), 8.57 (1H, d, J=5.2 Hz), 8.69 (1H, s).

Reference： [1]Patent: US2004/53908,2004,A1

37
[ 4972-29-6 ]
[ 3096-71-7 ]
[ 872675-95-1 ]

Reference： [1]Russian Journal of Organic Chemistry,2007,vol. 43,p. 1471 - 1474

38
[ 5184-27-0 ]
[ 3096-71-7 ]
[ 872675-95-1 ]

Reference： [1]Russian Journal of Organic Chemistry,2007,vol. 43,p. 1471 - 1474

39
[ 27691-42-5 ]
[ 3096-71-7 ]
[ 872675-99-5 ]

Reference： [1]Russian Journal of Organic Chemistry,2007,vol. 43,p. 1471 - 1474

40
[ 5184-31-6 ]
[ 3096-71-7 ]
[ 1057963-27-5 ]

Reference： [1]Russian Journal of Organic Chemistry,2007,vol. 43,p. 1471 - 1474

41
[ 5184-33-8 ]
[ 3096-71-7 ]
[ 1057963-27-5 ]

Reference： [1]Russian Journal of Organic Chemistry,2007,vol. 43,p. 1471 - 1474

42
[ 13088-17-0 ]
[ 3096-71-7 ]
[ 1057963-27-5 ]

Reference： [1]Russian Journal of Organic Chemistry,2007,vol. 43,p. 1471 - 1474

43
[ 13088-17-0 ]
[ 3096-71-7 ]
N-[(4-nitrophenyl)sulfinyl]-2,5-dimethyl-1,4-benzoquinone imine [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2008,vol. 44,p. 231 - 236

44
[ 3096-71-7 ]
[ 103-71-9 ]
[ 218134-92-0 ]

Reference： [1]Russian Journal of Organic Chemistry,2008,vol. 44,p. 1765 - 1772

45
[ 3096-71-7 ]
[ 3173-53-3 ]
[ 1174550-14-1 ]

Reference： [1]Russian Journal of Organic Chemistry,2008,vol. 44,p. 1765 - 1772

46
[ 624-78-2 ]
[ 3096-71-7 ]
[ 149-73-5 ]
N-ethyl-N'-(4-hydroxy-2,5-dimethylphenyl)-N-methylimidoformamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%		To a mixture of 10.0 g (73 mmol) of <strong>[3096-71-7]4-amino-2,5-dimethylphenol</strong> and 73 ml (0.84 mol) of trimethoxymethane 0.73 g (4.2 mmol) of p-toluene sulfonic acid were added and the mixture was heated to reflux for 2 hours. Then the volatiles were removed in vacuo and the residue was dissolved in 73 ml of toluene and 12.9 g (217 mmol) N-methylethanamine were added. The reaction mixture was heated to 5O0C for 20 hrs and concentrated in vacuo. Column chromatographie (gradient: cyclohexane -> ethyl acetate) yielded 9.17 g (44 mmol) 55 % of N- ethyl-N'-(4-hydroxy-2,5-dimethylphenyl)-N-methylimidoformamide; log P (pH 2.3) = 0.41.

Reference： [1]Patent: WO2007/31513,2007,A1 .Location in patent: Page/Page column 36

47
[ 1173435-16-9 ]
[ 3096-71-7 ]
[ 1173523-81-3 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 4173 - 4191

48
[ 57370-16-8 ]
[ 3096-71-7 ]
[ 1073844-73-1 ]

Yield	Reaction Conditions	Operation in experiment
		4-[(3-(tert-Butyl)-1,2,4-thiadiazol-5-yl)oxy]-2,5-dimethylaniline 754 mg (5.50 mmol) of 2,5-dimethyl-4-hydroxyaniline are dissolved in 5 ml of N,N-dimethylformamide and slowly treated with 242 mg (6.05 mmol) of sodium hydride. The reaction mixture is stirred for 15 min, before 972 mg (5.50 mmol) of 3-(tert-butyl)-5-chloro-1,2,4-thiadiazole are added. Subsequently, the reaction mixture is heated at 100 C. for 1 h and then cooled down to AT. After addition of 20 ml of ethyl acetate, the solution is extracted three times with water and dried over MgSO4, and the solvent is removed under vacuum (1.46 g, 94% purity, 90% yield, log P (pH 2.3)=3.29).

Reference： [1]Patent: US2010/105553,2010,A1 .Location in patent: Page/Page column 21-22

49
[ 1202783-63-8 ]
[ 3096-71-7 ]
[ 1202783-62-7 ]

Yield	Reaction Conditions	Operation in experiment
		4-[3-(3-Chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylaniline 3.86 g (28.1 mmol) of 2,5-dimethyl-4-hydroxyaniline are placed in 50 ml of acetonitrile, 4.66 g (33.8 mmol) of potassium carbonate are added at ambient temperature and the mixture is stirred for 30 min at ambient temperature. Subsequently, 11.0 g (28.1 mmol) of 3-(3-chlorobenzyl)-5-[(4-methylphenyl)sulphonyl]-1,2,4-thiadiazole are added and the reaction mixture is stirred at 50 C. for 12 h. After cooling, the mixture is concentrated using a rotary evaporator and the residue is taken in dichloromethane, extracted twice with water, dried over Na2SO4 and freed from the solvent under vacuum. 6.86 g of product are obtained (96.4% purity, 68.0% yield, log P (pH 2.3)=3.68).

Reference： [1]Patent: US2011/143937,2011,A1 .Location in patent: Page/Page column 31

50
[ 1202783-66-1 ]
[ 3096-71-7 ]
[ 1202783-65-0 ]

Yield	Reaction Conditions	Operation in experiment
76.9%		4-({3-[1-(4-Chlorophenyl)cyclopropyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylaniline 0.70 g (5.12 mmol) of 2,5-dimethyl-4-hydroxyaniline is placed in 18 ml of acetonitrile, 0.85 g (6.14 mmol) of potassium carbonate is added at ambient temperature and the mixture is stirred at ambient temperature for 30 min. Subsequently, 2.0 g (5.12 mmol) of 3-[1-(4-chloro-phenyl)cyclopropyl]-5-[(4-methylphenyl)sulphonyl]-1,2,4-thiadiazole are added and the reaction mixture is stirred at 50 C. for 12 h. After cooling, the reaction mixture is concentrated using a rotary evaporator and the residue is taken up in dichloromethane, extracted twice with water, dried over Na2SO4 and freed from the solvent under vacuum. 1.46 g of clean product are obtained (76.9% yield, log P (pH 2.3)=4.44).

Reference： [1]Patent: US2011/143937,2011,A1 .Location in patent: Page/Page column 32

51
[ 358-23-6 ]
[ 3096-71-7 ]
[ 1309965-22-7 ]

Reference： [1]Russian Journal of Organic Chemistry,2011,vol. 47,p. 510 - 519

52
[ 3096-71-7 ]
[ 124-63-0 ]
[ 321947-91-5 ]

Reference： [1]Russian Journal of Organic Chemistry,2011,vol. 47,p. 510 - 519

53
[ 1202783-63-8 ]
[ 3096-71-7 ]
[ 1202782-48-6 ]

Reference： [1]Patent: US2011/143937,2011,A1

54
[ 1202783-66-1 ]
[ 3096-71-7 ]
[ 1202782-50-0 ]

Reference： [1]Patent: US2011/143937,2011,A1

55
[ 1239257-77-2 ]
[ 3096-71-7 ]
[ 1239257-75-0 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium carbonate; In N,N-dimethyl-formamide; for 6h;Reflux;	Preparation of 5-(4-amino-2,5-dimethylphenoxy)-3-tert-butylisothiazole-4-carbonitrile A suspension of 5.0 g (24.9 mmol) of 3-tert-butyl-5-chloroisothiazole-4-carbonitrile, 3.41 g (24.9 mmol) of 2,5-dimethyl-4-hydroxyaniline and 5.51 g (39.86 mmol) of potassium carbonate in 100 ml of DMF is heated under reflux for 6 h. After cooling, the reaction mixture is poured onto ice-water. After extraction with dichloromethane, the combined organic phases are dried over Na2SO4 and freed from the solvent under reduced pressure.Purification by column chromatography on silica gel using cyclohexane/ethyl acetate gives 5.9 g (19.6 mmol, 79% of theory) of 5-(4-amino-2,5-dimethylphenoxy)-3-(4-chlorobenzyl)isothiazole-4-carbonitrile.

Reference： [1]Patent: US2011/130282,2011,A1 .Location in patent: Page/Page column 69-70

56
[ 1239257-80-7 ]
[ 3096-71-7 ]
[ 1239257-79-4 ]

Yield	Reaction Conditions	Operation in experiment
29%	With potassium carbonate; In N,N-dimethyl-formamide; for 6h;Reflux;	Preparation of 5-(4-amino-2,5-dimethylphenoxy)-3-(4-ehlorobenzyl)isothiazole-4-earbonitrile A suspension of 3.90 g (14.49 mmol) of 5-chloro-3-(4-chlorobenzyl)isothiazole-4-carbonitrile, 1.99 g (14.49 mmol) of 2,5-dimethyl-4-hydroxyaniline and 3.20 g (23.18 mmol) of potassium carbonate in 20 ml of DMF is heated under reflux for 6 h. After cooling, the reaction mixture is poured onto ice-water. After extraction with dichloromethane, the combined organic phases are dried over Na2SO4 and freed from the solvent under reduced pressure.Purification by column chromatography on silica gel using hexane/ethyl acetate gives 1.70 g (4.6 mmol, 29% of theory) of 5-(4-amino-2,5-dimethylphenoxy)-3-(4-chlorobenzyl)isothiazole-4-carbonitrile of logP(HCO2H)=4.03.

Reference： [1]Patent: US2011/130282,2011,A1 .Location in patent: Page/Page column 71

57
[ 1239257-80-7 ]
[ 3096-71-7 ]
[ 1239252-21-1 ]

Reference： [1]Patent: US2011/130282,2011,A1

58
[ 3096-71-7 ]
[ 21905-46-4 ]
[ 1239257-83-0 ]

Yield	Reaction Conditions	Operation in experiment
80%		Preparation of 2,5-dimethyl-4-[(3-phenylisothiazol-5-yl)oxy]aniline 0.34 g (8.43 mmol) of sodium hydride (60% in mineral oil) is added to a solution of 2,5-dimethyl-4-hydroxyaniline in 15 ml of DMF, and the reaction mixture is stirred at room temperature for 2 h. A solution of 1.50 g (7.67 mmol) of 5-chloro-3-phenylisothiazole in 5 ml of DMF is added dropwise to the reaction mixture. The reaction mixture is then stirred at 100 C. for 3 h. After cooling, the reaction mixture is added to ice-water and extracted with ethyl acetate. The combined organic phases are dried over Na2SO4 and freed from the solvent under reduced pressure.This gives 3.00 g (10.1 mmol, 80% of theory) of 2,5-dimethyl-4-[(3-phenylisothiazol-5-yl)oxy]aniline of logP(HCO2H)=3.60.

Reference： [1]Patent: US2011/130282,2011,A1 .Location in patent: Page/Page column 72-73

59
[ 1239257-86-3 ]
[ 3096-71-7 ]
[ 1239257-85-2 ]

Yield	Reaction Conditions	Operation in experiment
72%	With caesium carbonate; In N,N-dimethyl-formamide; at 150℃; for 4h;	Preparation of 4-[(4(4-chloro-3-phenylisothiazol-5-yl)oxy]-2,5-dimethylaniline A suspension of 300 mg (1.30 mmol) of 4,5-dichloro-3-phenylisothiazole, 179 mg (1.30 mmol) of 4-amino-2,5-dimethylbenzene and 680 mg (2.08 mmol) of caesium carbonate in 5 ml of N,N-dimethylformamide is stirred at 150 C. for 4 hours. After cooling, the reaction mixture is diluted with water and extracted with dichloromethane. The combined organic phases are dried over Na2SO4. The mixture is then filtered and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel using cyclohexane/ethyl acetate (3/1). This gives 310 mg (0.94 mmol, 72% of theory) of 4-[(4-chloro-3-phenylisothiazol-5-yl)oxy]-2,5-dimethylaniline of logP(HCO2H)=4.22.

Reference： [1]Patent: US2011/130282,2011,A1 .Location in patent: Page/Page column 73

60
[ 3096-71-7 ]
[ 1202781-91-6 ]

Reference： [1]Patent: US2012/71663,2012,A1
[2]Patent: US2012/71663,2012,A1

61
[ 3096-71-7 ]
[ 1357382-70-7 ]

Reference： [1]Patent: US2012/71663,2012,A1

62
[ 28860-25-5 ]
[ 3096-71-7 ]
[ 1357382-69-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With trichlorophosphate; In acetonitrile; at 60℃; for 1h;	At a maximum of 60 C., 9.2 g [60 mmol] of POCl3 are added dropwise to a solution of 6.86 g [50 mmol] of <strong>[3096-71-7]4-amino-2,5-dimethylphenol</strong> and 5.23 g [60 mmol] of N-ethyl-N-methylformamide in 20 ml of acetonitrile. After 1 hour at 60 C., the mixture is cooled to room temperature, concentrated to give a thick slurry, which is stirred with ca. 20 ml of cold isopropanol; the solid is filtered off with suction, washed with 10 ml of cold isopropanol and dried. This gives 10.4 g of a pale beige solid which, according to GC/MS (sil.) and HPLC, consists to 99.5% of N-ethyl-N'-(4-hydroxy-2,5-dimethylphenyl)-N-methylimidoformamide hydrochloride (yield=85% of theory).GC/MS (sil.): m/e=278 (M+, sil., 100%), 263 (M+, sil-Me, 70%), 205 (M+ sil-73, 20%).

Reference： [1]Patent: US2012/71663,2012,A1 .Location in patent: Page/Page column 17

63
[ 3096-71-7 ]
[ 149-73-5 ]
[ 1357382-71-8 ]

Yield	Reaction Conditions	Operation in experiment
83.8%	With toluene-4-sulfonic acid; for 2h;Reflux;	2.74 g [20 mmol] of <strong>[3096-71-7]4-amino-2,5-dimethylphenol</strong> are introduced into 20 ml of trimethyl orthoformate; 228 mg of para-toluenesulphonic acid hydrate are added and the mixture is heated at reflux for 2 hours. The reaction mixture is then concentrated by evaporation under reduced pressure, giving 4.9 g of a brown solid which, according to GC/MS analysis, consists to 61.3% of methyl (4-hydroxy-2,5-dimethylphenyl)imidoformate (83.8% of theory).GC/MS: m/e=179 (M+, 80%), 148 (M+-OMe, 100%).
	With toluene-4-sulfonic acid; for 1h;Reflux;	Reference prodution example 1 To 10 g of 4-hydroxy-2 , 5-dimethylaniline, 60 ml of trimethyl orthoformate and 1.4 g of para-toluenesulfonic acid monohydrate were added, and the mixture was refluxed for 1 hour. The reaction mixture was allowed to stand and cooled to about room temperature, then, to the reaction mixture, an aqueous saturated sodium hydrogen carbonate solution was added. The mixture was concentrated under reduced pressure. The resultant reesidue was washed with an aqueous saturated sodium hydrogen carbonate solution and mixed solvent of hexane and MTBE successtively, and gave 13 g of Methyl N- ( 4-hydroxy-2 , 5-dimethylphenyl ) formimidate . Methyl N- ( 4-hydroxy-2 , 5-dimethylphenyl) formimidate 1H-NMR (CDC13) delta: 2.17 (3H, s) , 2.19 (3H, s) , 3.87 (3H, s) , 6.55 (1H, s), 6.61 (1H, s) , 7.64 (1H, s) . To 13 g of Methyl N- ( 4-hydroxy-2 , 5- dimethylphenyl) formamidate, 200 ml of 1,4-dioxane was added at room temperature. To the mixture, 12 ml of ethylmethylamine was added at room temperature, and the mixture was stirred at 80C for 2 hours. The reaction mixture was allowed to stand and cooled to about room temperature, and concentrated under reduced pressure. The resulting solid was collected by filtration and washed with MTBE to obtain 8.1 g of N-ethyl- '-( 4-hydroxy-2 , 5- dimethylphenyl ) -N-methyformamidine . N-ethyl-N' - ( 4-hydroxy-2 , 5-dimethylphenyl) -N- methyformamidine 1H-NMR (CDCI3) delta: 1.19 (3H, t, J = 7.2 Hz), 2.18 (3H, s), 2.19 (3H, s), 2.97 (3H, s) , 3.34 (2H, br s) , 6.51 (1H, s) , 6.58 (1H, s) , 7.38 (1H, s) .

Reference： [1]Patent: US2012/71663,2012,A1 .Location in patent: Page/Page column 17
[2]Patent: WO2012/90969,2012,A1 .Location in patent: Page/Page column 154-156

64
[ 90418-16-9 ]
[ 3096-71-7 ]
[ 1357382-68-3 ]

Yield	Reaction Conditions	Operation in experiment
83.8%		Under an argon protective-gas atmosphere 2.74 g [20 mmol] of <strong>[3096-71-7]4-amino-2,5-dimethylphenol</strong> and 1.2 g [30 mmol] of NaOH (in the form of so-called micropills) are introduced into 15 ml of degassed and anhydrous DMAC. The mixture is stirred for 30 minutes at 40 C., then cooled to room temperature and then, with cooling at a maximum of 20 C., a solution of 4.9 g [10 mmol] of 5-chloro-3-(4-chlorobenzyl)-1,2,4-thiadiazole in 5 ml of degassed DMAC is added dropwise. After 2 hours at room temperature, the reaction mixture is filtered over some kieselguhr and then the filtrate is concentrated on a rotary evaporator at a maximum bath temperature of 50 C. in vacuo. The oil obtained in this way is stirred with ca. 50 ml of water. Extraction is carried out with in total about 100 ml of methylene chloride, and the combined organic phases are washed with water and dried over sodium sulphate. 6.9 g of brown oil result, which, according to HPLC analysis, consists to 84% of 4-[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylaniline (yield=83.8% of theory).LC/MS: m/e=346 (MH+).

Reference： [1]Patent: US2012/71663,2012,A1 .Location in patent: Page/Page column 16

65
[ 3096-71-7 ]
N'-(4-[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide hydrochloride [ No CAS ]

Reference： [1]Patent: US2012/71663,2012,A1

66
[ 24424-99-5 ]
[ 3096-71-7 ]
[ 185063-85-8 ]

Reference： [1]Patent: US2012/129890,2012,A1

67
[ 3096-71-7 ]
[ 929273-15-4 ]