[ CAS No. 28443-50-7 ] {[proInfo.proName]}

Name: 28443-50-7|2-Amino-5-chlorophenol|97%
Brand: Ambeed
SKU: A129726
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Quality Control of [ 28443-50-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 28443-50-7 ]

Product Details of [ 28443-50-7 ]

CAS No. :	28443-50-7	MDL No. :	MFCD02093863
Formula :	C₆H₆ClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FZCQMIRJCGWWCL-UHFFFAOYSA-N
M.W :	143.57	Pubchem ID :	91591
Synonyms :

Calculated chemistry of [ 28443-50-7 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	37.88
TPSA :	46.25 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.89 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.2
Log Po/w (XLOGP3) :	1.81
Log Po/w (WLOGP) :	1.64
Log Po/w (MLOGP) :	1.41
Log Po/w (SILICOS-IT) :	1.31
Consensus Log Po/w :	1.47

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.36
Solubility :	0.621 mg/ml ; 0.00433 mol/l
Class :	Soluble
Log S (Ali) :	-2.4
Solubility :	0.571 mg/ml ; 0.00397 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.06
Solubility :	1.26 mg/ml ; 0.00881 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.09

Safety of [ 28443-50-7 ]

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

Application In Synthesis of [ 28443-50-7 ]

* 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 [ 28443-50-7 ]
Downstream synthetic route of [ 28443-50-7 ]

[ 28443-50-7 ] Synthesis Path-Upstream 1~22

1
[ 28443-50-7 ]
[ 144-55-8 ]
[ 19219-99-9 ]

Reference： [1] Patent: EP318084, 1990, A3,
[2] Patent: EP318084, , A2, [2] Patent: , 1989, ,

2
[ 28443-50-7 ]
[ 144-55-8 ]
[ 19219-99-9 ]

Reference： [1] Patent: US4957932, 1990, A,

3
[ 28443-50-7 ]
[ 79-04-9 ]
[ 27320-99-6 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1984, vol. 23, # 12, p. 1279 - 1283
[2] Patent: WO2007/22257, 2007, A2, . Location in patent: Page/Page column 76

4
[ 28443-50-7 ]
[ 598-21-0 ]
[ 27320-99-6 ]

Reference： [1] ChemMedChem, 2015, vol. 10, # 11, p. 1821 - 1836

5
[ 1431459-74-3 ]
[ 28443-50-7 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 10, p. 2334 - 2337

6
[ 611-07-4 ]
[ 28443-50-7 ]

Reference： [1] Journal of the Chemical Society, 1928, p. 2703
[2] Fortsch.Ch.Phys., 1924, vol. 18, p. Heft 2,S.28
[3] Chemical Communications, 2011, vol. 47, # 39, p. 10972 - 10974

7
[ 328-50-7 ]
[ 932-98-9 ]
[ 62558-67-2 ]
[ 123-30-8 ]
[ 28443-50-7 ]
[ 81576-13-8 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 345 - 350

8
[ 932-98-9 ]
[ 305-72-6 ]
[ 62558-67-2 ]
[ 123-30-8 ]
[ 28443-50-7 ]
[ 81576-13-8 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 345 - 350

9
[ 932-98-9 ]
[ 305-72-6 ]
[ 62558-67-2 ]
[ 28443-50-7 ]
[ 81576-12-7 ]
[ 81576-13-8 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 345 - 350

10
[ 100-00-5 ]
[ 28443-50-7 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1966, p. 1848 - 1858

11
[ 16323-09-4 ]
[ 28443-50-7 ]

Reference： [1] Journal of Organic Chemistry, 1954, vol. 19, p. 758,762, 765

12
[ 5910-69-0 ]
[ 28443-50-7 ]

Reference： [1] Journal of Organic Chemistry, 1954, vol. 19, p. 758,762, 765

13
[ 74993-54-7 ]
[ 108-43-0 ]
[ 17609-80-2 ]
[ 56962-00-6 ]
[ 28443-50-7 ]

Reference： [1] Journal of the American Chemical Society, 1992, vol. 114, # 25, p. 9795 - 9806

14
[ 116278-63-8 ]
[ 17537-17-6 ]
[ 28443-50-7 ]
[ 116278-66-1 ]

Reference： [1] Journal of Organic Chemistry, 1995, vol. 60, # 25, p. 8294 - 8304

15
[ 139399-68-1 ]
[ 28443-50-7 ]

Reference： [1] Chemische Berichte, 1938, vol. 71, p. 2065,2069

16
[ 5467-64-1 ]
[ 28443-50-7 ]

Reference： [1] Chemische Berichte, 1938, vol. 71, p. 2065,2069

17
[ 95-55-6 ]
[ 28443-50-7 ]

Reference： [1] Chemische Berichte, 1938, vol. 71, p. 2065,2069

18
[ 116278-63-8 ]
[ 28443-50-7 ]
[ 554-00-7 ]
[ 116278-66-1 ]
[ 106-51-4 ]

Reference： [1] Journal of Organic Chemistry, 1988, vol. 53, # 20, p. 4762 - 4769

19
[ 116278-65-0 ]
[ 28443-50-7 ]
[ 116278-66-1 ]

Reference： [1] Journal of Organic Chemistry, 1988, vol. 53, # 20, p. 4762 - 4769

20
[ 28443-50-7 ]
[ 3621-82-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1975 - 1980
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3044 - 3049
[3] Journal of Fluorine Chemistry, 2013, vol. 156, p. 120 - 123
[4] Patent: WO2018/37223, 2018, A1,

21
[ 74993-54-7 ]
[ 108-43-0 ]
[ 17609-80-2 ]
[ 56962-00-6 ]
[ 28443-50-7 ]

Reference： [1] Journal of the American Chemical Society, 1992, vol. 114, # 25, p. 9795 - 9806

22
[ 28443-50-7 ]
[ 136808-72-5 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: With sulfuric acid; sodium nitrite In water; dimethyl sulfoxide at 0℃; for 1 h; Stage #2: With potassium iodide In water; dimethyl sulfoxide at 20℃; for 2 h;	Intermediate 15-Chloro-2-iodo-phenol 2-Amino-5-chlorophenol (5.7 g, 40 mmol) is dissolved in DMSO/water/H₂SO₄(200/60/140 mL) and cooled to 0° C. To this solution is added sodium nitrite (4.1 g, 60 mmol) in water (20 mL) and the mixture is stirred for 1 h at 0° C. To the mixture is added potassium iodide (19.9 g, 120 mmol) in water (20 mL) and the mixture is stirred at room temperature for 1 h. Another batch of potassium iodide (19.9 g, 120 mmol) in water (20 mL) is added and the mixture is stirred at room temperature for 1 h. The mixture is diluted with ethyl acetate, washed with water, saturated aqueous sodium sulfate, and brine. The organic portion is dried over MgSO₄, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (Biotage.(TM). Si65M, 20percent ethyl acetate/hexane) to yield 8.09 g (79percent) of the title compound as a pink solid. GCMS m/e 254 [M]^-.

Reference： [1] Patent: US2010/69425, 2010, A1, . Location in patent: Page/Page column 11-12
[2] Journal of the Chemical Society, 1931, p. 2268,2271

[ 28443-50-7 ] Synthesis Path-Downstream 1~52

1
[ 611-07-4 ]
[ 28443-50-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 4225 - 4229
[2]Journal of the Chemical Society,1928,p. 2703
[3]Fortschritte der Chemie, Physik und physikalischen Chemie,1924,vol. 18,p. Heft 2,S.28
[4]Chemical Communications,2011,vol. 47,p. 10972 - 10974

2
[ 506-68-3 ]
[ 28443-50-7 ]
[ 52112-68-2 ]

Reference： [1]Journal of the Chemical Society,1956,p. 4727,4730
[2]International Journal of Molecular Sciences,2020,vol. 21

3
[ 44830-55-9 ]
[ 28443-50-7 ]
[ 100126-53-2 ]
[ 52112-68-2 ]

Reference： [1]Journal of the Chemical Society,1956,p. 4727,4730

4
[ 28443-50-7 ]
[ 136808-72-5 ]

Yield	Reaction Conditions	Operation in experiment
79%		Intermediate 15-Chloro-2-iodo-phenol 2-Amino-5-chlorophenol (5.7 g, 40 mmol) is dissolved in DMSO/water/H2SO4 (200/60/140 mL) and cooled to 0 C. To this solution is added sodium nitrite (4.1 g, 60 mmol) in water (20 mL) and the mixture is stirred for 1 h at 0 C. To the mixture is added potassium iodide (19.9 g, 120 mmol) in water (20 mL) and the mixture is stirred at room temperature for 1 h. Another batch of potassium iodide (19.9 g, 120 mmol) in water (20 mL) is added and the mixture is stirred at room temperature for 1 h. The mixture is diluted with ethyl acetate, washed with water, saturated aqueous sodium sulfate, and brine. The organic portion is dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (Biotage Si65M, 20% ethyl acetate/hexane) to yield 8.09 g (79%) of the title compound as a pink solid. GCMS m/e 254 [M]-.

Reference： [1]Patent: US2010/69425,2010,A1 .Location in patent: Page/Page column 11-12
[2]Journal of the Chemical Society,1931,p. 2268,2271

5
[ 74993-54-7 ]
[ 108-43-0 ]
[ 17609-80-2 ]
[ 56962-00-6 ]
[ 28443-50-7 ]

Reference： [1]Journal of the American Chemical Society,1992,vol. 114,p. 9795 - 9806

6
[ 28443-50-7 ]
[ 79-04-9 ]
[ 27320-99-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 - 80℃;	A mixture of 2-amino-5-chloro- phenol (27) (2.0 g, 14 mmol, 1 equiv) in 30 ml of THF, chloroacetyl chloride (1.26 ml, 16.8 mmol, 1.2 equiv), and saturated aqueous NaHCO3 50 mL was stirred at RT for 2 hrs and then heated at 80 0C overnight. The reaction mixture was diluted with EtOAc, and washed with water. Purification of the crude product by flash chromatography provided 7-chloro-4H- benzo[l,4]oxazin-3-one (28): LCMS Retention time: 1.48 min.; LCMS observed (M+H)+: 184.

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1984,vol. 23,p. 1279 - 1283
[2]Patent: WO2007/22257,2007,A2 .Location in patent: Page/Page column 76

7
[ 140-89-6 ]
[ 28443-50-7 ]
[ 22876-20-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: potassium ethyl xanthogenate; 2-amino-5-chlorophenol In PEG 400 at 165℃; for 0.1h; Microwave irradiation; Stage #2: With acetic acid In ethanol; water; PEG 400
	In ethanol Heating;

Reference： [1]Location in patent: experimental part Deligeorgiev, Todor G.; Kaloyanova, Stefka S.; Lesev, Nedyalko Y.; Vaquero, Juan J. [Monatshefte fur Chemie, 2011, vol. 142, # 9, p. 895 - 899]
[2]Tully, David C.; Liu, Hong; Alper, Phil B.; Chatterjee, Arnab K.; Epple, Robert; Roberts, Michael J.; Williams, Jennifer A.; Nguyen, Khanhlinh T.; Woodmansee, David H.; Tumanut, Christine; Li, Jun; Spraggon, Glen; Chang, Jonathan; Tuntland, Tove; Harris, Jennifer L.; Karanewsky, Donald S. [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1975 - 1980]

8
[ 18355-73-2 ]
[ 28443-50-7 ]
[ 908336-75-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran at 0 - 20℃;

Reference： [1]Smits, Rogier A.; Lim, Herman D.; Stegink, Bart; Bakker, Remko A.; De Esch, Iwan J. P.; Leurs, Rob [Journal of Medicinal Chemistry, 2006, vol. 49, # 15, p. 4512 - 4516]

9
[ 28443-50-7 ]
[ 3621-82-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1975 - 1980
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3044 - 3049
[3]Journal of Fluorine Chemistry,2013,vol. 156,p. 120 - 123
[4]Patent: WO2018/37223,2018,A1

10
[ 28443-50-7 ]
[ 230955-75-6 ]
[ 1056010-66-2 ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol; at 85℃; for 4h;	A mixture of intermediate 85 (0.00696 mol) and 2-AMINO-5-CHLORO-PHENOL (0.00696 mol) in 2-propanol (100 ml) was heated under stirring for 4 hours at 85C and the reaction mixture was cooled to RT, then the resulting precipitate was filtered off, yielding intermediate 86, isolated as A MONOHYDROCHLORIC ACID.

Reference： [1]Patent: WO2004/105765,2004,A1 .Location in patent: Page 90

11
[ 68281-43-6 ]
[ 28443-50-7 ]
[ 74-88-4 ]
[ 534571-82-9 ]

Yield	Reaction Conditions	Operation in experiment
		4.a Step a Step a 6-Chloro-2-ethoxycarbonyl-4-methyl-2H-1,4-benzoxazine The expected product is obtained in accordance with the process described in Example 1, Step a, replacing iodopropane by iodomethane and using 6-chloro-2-ethoxycarbonyl-3,4-dihydro-2H-1,4-benzoxazine (prepared in accordance with the process described in J. Heterocyclic Chem., 1985, 22, 177, starting from 2-hydroxy-4-chloroaniline) as starting material.

Reference： [1]Current Patent Assignee: SERVIER MONDE - US6057317, 2000, A

12
P₂ O₅ [ No CAS ]
[ 28443-50-7 ]
[ 144-55-8 ]
[ 19219-99-9 ]

Yield	Reaction Conditions	Operation in experiment
	With methanesulfonic acid; In acetic acid; ethyl acetate; toluene;	Step 2 Preparation of 5-chloro-2-methylbenzoxazole To a solution of P2 O5 (1 g) and methanesulphonic acid (10 g) was added 2-amino-5-chlorophenol (1.6 g) and glacial acetic acid (570 muL). The reaction mixture was stirred at 70 C. overnight and then at 90 for 4 hours. The mixture was poured into a well stirred saturated aqueous NaHCO3 solution (200 mL) and extracted with EtOAc (3x). The organic extracts were dried and evaporated. Purification of the residue by column chromatography using toluene/EtOAc (10:0.2) as eluant afforded the title compound as a pink solid.

Reference： [1]Patent: US4957932,1990,A

13
[ 28443-50-7 ]
[ 144-55-8 ]
[ 19219-99-9 ]

Yield	Reaction Conditions	Operation in experiment
	With P2O5; methanesulfonic acid; In acetic acid; ethyl acetate; toluene;	Step 2 Preparation of 5-chloro-2-methylbenzoxazole To a solution of P2O5 (1 g) and methanesulphonic acid (10 g) was added 2-amino-5-chlorophenol (1.6 g) and glacial acetic acid (570 muL). The reaction mixture was stirred at 70C overnight and then at 90 for 4 hours. The mixture was poured into a well stirred saturated aqueous NaHCO3 solution (200 mL) and extracted with EtOAC (3x). The organic extracts were dried and evaporated. Purification of the residue by column chromatography using toluene/EtOAC (10:0.2) as eluant afforded the title compound as a pink solid.

Reference： [1]Patent: EP318084,A2
Patent: ,1989,

14
[ 28443-50-7 ]
[ 74974-54-2 ]
6-chloro-2-(chloromethyl)benzo[d]oxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid for 1h; Reflux;	6.a To 2-amino-5-chloro-phenol (2.5 g) in acetic acid (25 mL) was added 2-chloro- 1,1,1 - trimethoxy-ethane (3.23 g) and the mixture heated under reflux for Ih. The solvent was removed under vacuum and the residue purified by chromatography on silica gel using diethyl ether / isohexane (1 : 10) to afford the sub-titled compound as a solid (2.60 g).1H NMR (400 MHz, CDCl3) Î' 7.58 (IH, d), 7.36 (IH, dd), 7.66 (IH, d), 4.74 (2H, s).

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC; CHARLES RIVER LABORATORIES INTERNATIONAL INC - WO2009/153536, 2009, A1 Location in patent: Page/Page column 39

15
[ 28443-50-7 ]
[ 619-41-0 ]
[ 80306-38-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-amino-5-chlorophenol With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In dichloromethane; water for 0.5h; Stage #2: 4-(bromoacetyl)toluene In dichloromethane; water for 12.25h;
	Stage #1: 2-amino-5-chlorophenol With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In dichloromethane; water at 20℃; for 2h; Stage #2: 4-(bromoacetyl)toluene In dichloromethane; water Reflux;	A General procedure: [0081] General Procedure for the Preparation of Atypical Retinoids (AR1-AR10)50 (FIG. 4b and Table 1): [0082] The 2H-benzo[b][1,4]oxazines were synthesized by modifying the existing methods. To a solution of 2-aminophenol (0.001 mol) in dichloromethane (40 ml) aqueous potassium carbonate (20% w/v) and tetrabutylammonium hydrogen sulfate (0.0005 mol) was added and mixture was stirred for 2 h at room temperature. After 2 h, 2-bromo-4-chloroacetophenone (0.01 mol) in 20 ml dichloromethane was added drop-wise through a course of 15 min and the resultant mixture was refluxed till completion for 4-6 h. The organic layer was extracted with dichloromethane and dried over sodium sulfate evaporated in vacuum to give crude solid product. The solid was then recrystallized with hot ethanol to get pure yield 87-95%.

Reference： [1]Das, Bhaskar C.; Madhukumar, Ankanahlli V.; Anguiano, Jaime; Mani, Sridhar [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 15, p. 4204 - 4206]
[2]Current Patent Assignee: MONTEFIORE MEDICAL CENTER - US2015/166492, 2015, A1 Location in patent: Paragraph 0081; 0082; 0122

16
[ 53911-68-5 ]
[ 28443-50-7 ]
[ 1221962-68-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	In dichloromethane; for 0.5h;	Prepared by refluxing an equimolar mixture of <strong>[53911-68-5]3-(4-chlorophenyl)glutaric anhydride</strong> and commercial 4-chloro-2-hydroxyaniline in dichloromethane for 0.5 h. After cooling to rt the precipitated product is isolated by suction filtration, washed, and dried to provide 90% of Lambda/-(2-hydroxy-4-chlorophenyl)-3-(4-chlorophenyl)glutaramic acid as light red crystals.
90%	In dichloromethane; for 0.5h;	Prepared by refluxing an equimolar mixture of <strong>[53911-68-5]3-(4-chlorophenyl)glutaric anhydride</strong> and commercial 4-chloro-2-hydroxyaniline in dichloromethane for 0.5 h. After cooling to rt the precipitated product is isolated by suction filtration, washed, and dried to provide 90% of N-(2-hydroxy-4-chlorophenyl)-3-(4-chlorophenyl)glutaramic acid as light red crystals. 2

Reference： [1]Patent: WO2010/43711,2010,A1 .Location in patent: Page/Page column 92
[2]Patent: US2012/46307,2012,A1 .Location in patent: Page/Page column 44

17
[ 1850-14-2 ]
[ 28443-50-7 ]
[ 57260-71-6 ]
[ 1092847-79-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With acetic acid In chloroform at 60℃;	2 In accordance with the invention, substituted 2-aminobenzoxazoles can be prepared in one pot using commercially available tetramethyl orthocarbonate (2 eq, Aldrich), an amine (2 eq), and an optionally substituted 2-aminophenol (1 eq). The reaction maybe carried out in the presence of acetic acid (4 eq) in chloroform at 60°C (using a sealed tube for volatile amines). Tetramethyl orthocarbonate can be successfully replaced by its tetraethyl analogue in this reaction. Other useful solvents for the reaction include methanol, ethanol, isopropyl alcohol, acetonitrile, tetrahydrofuran, ethyl acetate, toluene, and combinations thereof.The mild reaction conditions permit the reaction to be applied to compounds with sensitive functional groups, for example, esters. The reaction is clean, providing virtually spot-to-spot conversion from an aminophenol to a 2-methoxybenzoxazole to a 2-aminobenzoxazole. The work-up and purification is straightforward and easy; in many cases, a simple re-crystallization may be sufficient for purification of final compounds. The reaction is versatile, as is demonstrated by the variety of amine reactants listed in TABLE 1. As shown by the structures included in TABLE 2, electron donating and withdrawing substituents on the 2-aminophenol are also well tolerated. The reaction by-products are methanol and, optionally, acetic acid. A simplified work-up may only involve concentration under reduced pressure, which makes the reaction particularly amenable to large-scale production. The reaction can be carried out in a variety of solvents, including methanol, acetonitrile, tetrahydrofuran, ethyl acetate, and toluene. Optionally, the solvent may include an acid such as acetic acid. However the reaction proceeds in good yield in chloroform without acetic acid.
99%	Stage #1: tetramethoxymethane; 2-amino-5-chlorophenol; 1-t-Butoxycarbonylpiperazine With acetic acid In chloroform at 60℃; for 16h; Inert atmosphere; Stage #2: With sodium hydroxide In chloroform; water at 20℃; Inert atmosphere;

Reference： [1]Current Patent Assignee: CURIA INC - WO2010/48514, 2010, A1 Location in patent: Page/Page column 9
[2]Cioffi, Christopher L.; Lansing, John J.; Yueksel, Hamza [Journal of Organic Chemistry, 2010, vol. 75, # 22, p. 7942 - 7945]

18
[ 75-15-0 ]
[ 28443-50-7 ]
[ 22876-20-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium hydroxide In ethanol at 90℃; for 2h;	6-Chlorobenzo[d]oxazole-2-thiol To a solution of KOH (4.7g, 83.8mmol) in EtOH (lOOmL) were added 2-amino-5- chlorophenol (4.Og, 27.8mmol) and CS2 (5.lOmL, 83.8mmol) at rt. The reaction mixture was refluxed for 2 h. TLC showed the reaction to be complete. The solvent was removed under reduced pressure to give the crude residue. The residue was acidified with iON HCI (lOOmL) and extracted with EtOAc (3xlOOmL). The organic layer was washed with brine (lOOmL), dried (Na2504), filtered and concentrated under reduced pressure to afford 6-chlorobenzo[d]oxazole-2-thiol as an off-white solid. Yield: 4.6 g (89%); 1H NMR (400 MHz, DMSO-d6): O 14.02 (bs, 1H), 7.73 (5, 1H), 7.34 (d, J = 8.4 Hz, 1H), 7.23 (d, J = 8.4 Hz, 1H); MS (ESl+) for CHNOS m/z185.97 [M+H]
80%	With potassium hydroxide In ethanol; water for 72h; Inert atmosphere; Reflux;	6-chlorobenzo[d]oxazole-2-thiol (KR-200Cl) Potassium hydroxide (44.51 mol, 2.50 g) was added to a solution of 2-amino-5-chlorophenol (40.47 mmol, 5.81 g) in carbon disulfide (80.94 mmol, 4.89 mL), ethanol (34.0 mL) and water (6.7 mL) with constant magnetic stirring. The reaction was placed under argon atmosphere and refluxed for 72 hours. The reaction mixture is then cooled to room temperature and filtered. The filtrand is then rinsed with ice cold ethanol (10 mL), transferred to a separatory funnel, acidified with 1N hydrochloric acid (150 mL), and extracted with ethyl acetate (6 x 160 mL). The organic layer was then dried over sodium sulfate and concentrated under reduced pressure yielding an orange solid. Silica gel column chromatography of the solid (2:1 hexanes/chloroform) provided pure KR-200Cl as a white crystalline solid in an 80% yield.
	With potassium carbonate In ethanol; water for 3h; Reflux;	1.1.General Procedure for the Synthesis of compound 2 General procedure: The substituted 2-aminophenol (1eq.) in water and 95% ethanol was added potassium carbonate (1eq.) and CS2 (1eq.).The mixture was heated under reflux for 3 hours. After cooling, the solution was neutralized with 15 mL of acetic acid in 30 mL water. The precipitate was collected to give 2-thiolbenzoxazoles. Then, the substituted 2-thiolbenzoxazoles (1eq.) dissolved in toluene, PCl5 (1.5eq) was added dropwise. The mixture was heated to reflux for 2 hours. After the solvent was evaporated, the crude product was purified by silica gel column chromatography using PE-EA as an eluent.

	With potassium hydroxide In ethanol; water for 4.25h; Reflux;	4.1. General procedure General procedure: Potassium hydroxide (46 mmol), ethanol (25 mL) and water (10 mL) were added to a dried round-bottomed flask sequentially, followed by the dropwise addition of CS2 (25 mmol), after 15 min, (un)substituted 2-aminophenol (23 mmol) was added, then the resulting solution was heated to reflux for 4 h. The reaction solution was acidified to pH~4 with dilute hydrochloric acid and then poured into water, extracted with ethyl acetate, the organic phase was washed with brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure and the residue was purified via silica gel column chromatography to obtain the intermediate the (un)substituted 2-mercaptobenzoxazole as a yellow solid. Then, the (un)substituted 2-mercaptobenzoxazole (5.5 mmol) was refluxed in SOCl2 (15 mL) for 2 h, excessive SOCl2 was removed under reduced pressure to give (un)substituted 2-chlorobenzoxazole as a yellow solid which was used in next reaction without further purification. Finally, 60 % of NaH (1.0 mmol) was added into a solution of 3,3-dichloroallyloxyphe-noxy intermediates (1.0 mmol) in THF (5 mL), after 2 h, (un)substituted 2-chloro-benzoxazole (1.0 mmol) was added, the reaction mixture was stirred for another 5 h at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate, the organic phase was washed with saturated sodium bicarbonate, brine, dried over anhydrous magnesium sulfate, concentrated and the residue was purified via silica gel column chromatography to afford the title compounds.
	Stage #1: 2-amino-5-chlorophenol With sodium hydroxide In water at 95 - 100℃; for 3h; Stage #2: carbon disulfide at 75 - 80℃; for 13h;	1.1; 1.11-1.17; 2.1; 2.11-2.17; 3.1; 3.11-3.17 S1: Preparation of mercapto-6-chlorobenzoxazole; S11: Put the solid wet material monochloride, water and caustic soda into the alkaline hydrolysis kettle; S12: React for 3 hours at a kettle temperature of 95100; S13: Open the cooling water of the alkaline hydrolysis kettle to lower the temperature, and use vacuum to feed the sulfhydryl kettle at 60°C; S14: After the alkaline hydrolysis solution is fed to the sulfhydryl kettle, open the steam valve and turn off the steam when the temperature reaches 75°C; open the bottom valve of the carbon disulfide metering tank, slowly drip carbon disulfide into the sulfhydryl kettle, control the kettle temperature at 75°C, and react for 10 hours. ; Keep at 80 °C for 3 hours; S15: After the heat preservation reaction is over, open the steam valve, slowly heat up the distillation to recover carbon disulfide, until there is basically no reflux; turn off the steam, and use a pump to pump into the acidification kettle when the temperature is lowered to 60°C; S16: Slowly add hydrochloric acid dropwise to the acidification kettle, and react for 3 hours; S17: The dripping ends when the pH value is 2; after cooling, the material is pumped into the sulfhydryl transfer kettle and the material is discharged and centrifuged to obtain the intermediate 2-mercapto-6-chlorobenzoxazole.

Reference： [1]Current Patent Assignee: SUMMIT THERAPEUTICS PLC - WO2018/37223, 2018, A1 Location in patent: Page/Page column 197
[2]Rynearson, Kevin D.; Charrette, Brian; Gabriel, Christopher; Moreno, Jesus; Boerneke, Mark A.; Dibrov, Sergey M.; Hermann, Thomas [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 15, p. 3521 - 3525]
[3]Ouyang, Liang; Huang, Yuhui; Zhao, Yuwei; He, Gu; Xie, Yongmei; Liu, Jie; He, Jun; Liu, Bo; Wei, Yuquan [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3044 - 3049]
[4]Guan, Aiying; Qin, Yukun; Wang, Junfeng; Li, Bin [Journal of Fluorine Chemistry, 2013, vol. 156, p. 120 - 123]
[5]Current Patent Assignee: JIANGSU YONG KAI CHEM - CN113185475, 2021, A Location in patent: Paragraph 0032-0040; 0053-0062; 0076-0084

19
[ 28443-50-7 ]
[ 113100-53-1 ]
[ 1428626-97-4 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere;	General procedure: To a solution of carboxylic acid (1 equiv) in CH2Cl2 or DMF (1 mL) was added HOBt (1.2 equiv) and DIEA (2 equiv). After the mixture was stirred at room temperature for 5 min, EDCI (1.1 equiv) and corresponding amine (1.3 equiv) were added. The mixture was stirred overnight, diluted with ethyl acetate (40 mL), washed with 1 N HCl (10 mL), saturated NaHCO3 (20 mL), H2O (20 mL), brine (20 mL), dried over Na2SO4, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2035 - 2043

20
[ 28443-50-7 ]
[ 848133-76-6 ]

Reference： [1]Heterocycles,2014,vol. 89,p. 1203 - 1209

21
[ 28443-50-7 ]
[ 7424-54-6 ]
[ 1027019-12-0 ]

Yield	Reaction Conditions	Operation in experiment
66%	With copper(l) iodide; toluene-4-sulfonic acid In acetonitrile at 100℃; for 16h;

Reference： [1]Mayo, Muhammad Shareef; Yu, Xiaoqiang; Zhou, Xiaoyu; Feng, Xiujuan; Yamamoto, Yoshinori; Bao, Ming [Journal of Organic Chemistry, 2014, vol. 79, # 13, p. 6310 - 6314]

22
[ 82294-70-0 ]
[ 28443-50-7 ]
[ 68-11-1 ]
[ 1620166-78-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With acetic acid; In N,N-dimethyl-formamide; at 110℃; for 0.166667h;Microwave irradiation;	General procedure: An equimolar amount of substituted aldehydes (1a-n) (1 mmol), 2-amino-5-chlorophenol (2) (1 mmol), thioglycolic acid (3) (1 mmol) were added in DMF, with 2-3 drops of glacial acetic acid. This mixture was taken in a 100 mL round bottom flask subjected to MW irradiation (800 W), at 110 C temperature for 8-10 min. The completion of the reaction progress was monitored by using TLC (5 % Ethyl acetate: n-hexane). The product obtained was poured into crushed ice, filtered and extracted with petroleum ether and ethyl acetate (2:8), (3×10 mL). The combined solvents extracted were concentrated in vacuo. The compounds were recrystallized from ethanol to obtain pure product (4a-n).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3569 - 3573

23
[ 93614-80-3 ]
[ 28443-50-7 ]
[ 623-47-2 ]
7-chloro-2-m-tolyl-1,9a-dihydro-2H-9-oxa-4a-azafluorene-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 7232 - 7238

24
[ 28443-50-7 ]
[ 104619-51-4 ]
[ 52112-68-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	In acetonitrile; for 8h;Inert atmosphere; Reflux;	Di(imidazole-1-yl)methanimine (10.49 mmol, 1.69 g) was added to a solution of 2-amino-5-chlorophenol (3.50 mmol, 0.50 g) in acetonitrile (50 mL) with constant magnetic stirring. The reaction was then placed under argon atmosphere and gently refluxed for eight hours. The reaction was then concentrated under reduced pressure and silica gel column chromatography (3:1 hexanes/ethyl acetate) provided a crystalline white solid in an 86% yield.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3521 - 3525

25
[ 17347-32-9 ]
[ 28443-50-7 ]
[ 82102-37-2 ]
2-(benzothiophen-6-yl)-6-chlorobenzoxazole [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2094 - 2097

26
[ 19213-72-0 ]
[ 28443-50-7 ]
[ 19932-84-4 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 59594 - 59602

27
[ 55305-43-6 ]
[ 28443-50-7 ]
[ 52112-68-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at 5 - 20℃; for 1h;Green chemistry;	General procedure: To a solution of o-aminophenol (400 mg, 3.67 mmol) and NCTS (998 mg, 3.67 mmol) in THF (6 mL), 1 M LiHMDS in hexane (3.67 mL, 3.67 mmol) was added and stirred at 5 C to r.t. for 1h. Then the reaction mixture was poured in ice water and stirred for 15 min. Then extracted with EtOAc, the organic layer was separated. The organic layer was washed with brine solution.Then organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to obtained pure 2-aminobenzaxozole in 90% yield (471 mg).

Reference： [1]Synlett,2015,vol. 26,p. 897 - 900

28
[ 881668-70-8 ]
[ 28443-50-7 ]
[ 1073468-92-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3024 - 3029

29
[ 115964-19-7 ]
[ 28443-50-7 ]
[ 1073468-93-5 ]

Yield	Reaction Conditions	Operation in experiment
	With polyphosphoric acid at 160℃; for 18h;

Reference： [1]Pelcman, Benjamin; Sanin, Andrei; Nilsson, Peter; No, Kiyo; Schaal, Wesley; Öhrman, Sara; Krog-Jensen, Christian; Forsell, Pontus; Hallberg, Anders; Larhed, Mats; Boesen, Thomas; Kromann, Hasse; Vogensen, Stine Byskov; Groth, Thomas; Claesson, Hans-Erik [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 3024 - 3029]

30
[ 28443-50-7 ]
[ 598-21-0 ]
[ 27320-99-6 ]

Reference： [1]ChemMedChem,2015,vol. 10,p. 1821 - 1836

31
[ 28443-50-7 ]
[ 107-02-8 ]
[ 5622-06-0 ]

Yield	Reaction Conditions	Operation in experiment
73%	With hydrogenchloride; sodium hydroxide In water for 2h; Reflux;

Reference： [1]Thinnes; Tumber; Yapp; Scozzafava; Yeh; Chan; Tran; Hsu; Tarhonskaya; Walport; Wilkins; Martinez; Müller; Pugh; Ratcliffe; Brennan; Kawamura; Schofield [Chemical Communications, 2015, vol. 51, # 84, p. 15458 - 15461]

32
[ 17282-03-0 ]
[ 201230-82-2 ]
[ 28443-50-7 ]
9-chloro-3-methylbenzo[b]pyrido[3,2-f ][1,4]oxazepin-5(6H)-one [ No CAS ]

Reference： [1]Catalysis Science and Technology,2015,vol. 5,p. 4433 - 4443

33
[ 201230-82-2 ]
[ 28443-50-7 ]
[ 185017-72-5 ]
9-chloro-2-methylbenzo[b]pyrido[3,2-f ][1,4]oxazepin-5(6H)-one [ No CAS ]

Reference： [1]Catalysis Science and Technology,2015,vol. 5,p. 4433 - 4443

34
[ 28443-50-7 ]
[ 530-62-1 ]
[ 19932-84-4 ]

Yield	Reaction Conditions	Operation in experiment
78.4%	In tetrahydrofuran for 4h; Reflux;	2 4.1.2. General procedure for the synthesis of 6-substitutedbenzo[d]oxazol-2(3H)-ones (5a-c) General procedure: To a stirred solution of appropriate aminophenol (4a-c) (1 mmol) in dry tetrahydrofuran (THF) (20 mL) was added 1,1'-carbonyldiimidazole (CDI) (1.1 mmol) at room temperature (rt). The solution was refluxed for about 4 h (monitored by TLC & LCMS for completion), and solvent evaporated under reduced pressure.16 The residue was further diluted with water (20 mL) and ethyl acetate (20 mL) and the layers separated. The organic layer was washed with 2 N hydrochloric acid (15 mL), water (10 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography using hexane: ethyl acetate as eluent to give the corresponding benzoxazolone (5a-c) in good yield.
	In N,N-dimethyl-formamide at 60℃; for 2h;

Reference： [1]Pedgaonkar, Ganesh S.; Sridevi, Jonnalagadda Padma; Jeankumar, Variam Ullas; Saxena, Shalini; Devi, Parthiban Brindha; Renuka, Janupally; Yogeeswari, Perumal; Sriram, Dharmarajan [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 21, p. 6134 - 6145]
[2]Bach, Anders; Pizzirani, Daniela; Realini, Natalia; Vozella, Valentina; Russo, Debora; Penna, Ilaria; Melzig, Laurin; Scarpelli, Rita; Piomelli, Daniele [Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9258 - 9272]

35
[ 32315-10-9 ]
[ 28443-50-7 ]
[ 19932-84-4 ]

Yield	Reaction Conditions	Operation in experiment
66%	With pyridine In tetrahydrofuran at 5 - 20℃; for 3.5h;

Reference： [1]Zhang, Hao; Liu, Kechang; Liu, Ruiquan; Li, Qibo; Li, Yongqiang; Wang, Qingmin; Liu, Shangzhong [Chinese Journal of Chemistry, 2015, vol. 33, # 7, p. 749 - 755]

36
[ 608-21-9 ]
[ 28443-50-7 ]
C₁₂H₇BrClNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With polyphosphoric acid; at 180℃; for 4h;	2-amino-5-chlorophenol (3.0 g, 0.014 mol) in <strong>[608-21-9]1,2,3-tribromobenzene</strong> (4.4 g, 0.014 mol) into a PPA (polyphosphoric acid) into 100 mL to 180 C 4 hours reaction was stirred. After the reaction cooled H20: MC column purification (n-Hexane: MC) to give the intermediate 25-1 2.1 g (51%) (m / z = 296).

Reference： [1]Patent: KR2015/133097,2015,A .Location in patent: Paragraph 0555; 0556

37
[ 608-21-9 ]
[ 28443-50-7 ]
C₁₃H₆BrClN₂O [ No CAS ]

Reference： [1]Patent: KR2015/133097,2015,A

38
[ 28443-50-7 ]
[ 446-30-0 ]
C₁₃H₈Cl₂FNO₂ [ No CAS ]

Reference： [1]Pharmacological Research,2016,vol. 113,p. 610 - 625

39
ammonium thiocyanate [ No CAS ]
[ 28443-50-7 ]
[ 52112-68-2 ]

Yield	Reaction Conditions	Operation in experiment
32%		Preparation of 6-chlorobenzoxazol-2-amine: 5.0 g (0.035 mol) of 2-amino-5-chlorophenol,Ammonium thiocyanate 4.0 g (0.053 mol)Was added to a 100 ml round bottom flask,Then, 30 ml of 0.053 mol of hydrochloric acid was added,Reflow 6h.Let cool.Ethyl acetate 30 ml x 3 Extraction acid aqueous phase,Combine organic phase,Dried over anhydrous sodium sulfate for 12 h.The product was evaporated to dryness and dissolved in 40 ml of methanol.11.9 g (0.053 mol) of lead oxide was added,Reflux 8h,Hot filter,Get a black liquid.Recovery solvent,Column separation,Dichloromethane: methanol = 30: 1,Get brown red solid,1.89g,M.p. 176 to 178 C,Yield: 32.0%.

Reference： [1]Patent: CN103772376,2017,B .Location in patent: Paragraph 0124; 0125

40
[ 137-26-8 ]
[ 28443-50-7 ]
[ 22876-20-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	In water at 80℃; Green chemistry;
68%	Stage #1: 2-amino-5-chlorophenol With potassium carbonate In N,N-dimethyl-formamide for 0.0833333h; Stage #2: Thiram In N,N-dimethyl-formamide at 120℃; for 12h;	Typical procedure for the preparation of 2-mercaptobenzoxazoles in the presence of K2CO3 (TP2) General procedure: 2-Aminophenol (1.0 mmol), K2CO3 (3.0 mmol) was dissolved in DMF (3 mL) in a dried tube, equipped with a magnetic stirring bar and a septum. The mixture was stirred for 5 minutes, and then TMTD (0.6 mmol) was added. The reaction mixture was then heated at 120 °C and checked by TLC until the starting material was finished (around 12 hours). The reaction was cooled down to room temperature, and then quenched with sat. NH4Cl solution and extracted with ethyl acetate, dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flash column chromatography to afford the desired product.

Reference： [1]Liu, Xing; Liu, Min; Xu, Wan; Zeng, Meng-Tian; Zhu, Hui; Chang, Cai-Zhu; Dong, Zhi-Bing [Green Chemistry, 2017, vol. 19, # 23, p. 5591 - 5598]
[2]Liu, Min; Zeng, Meng-Tian; Xu, Wan; Wu, Li; Dong, Zhi-Bing [Tetrahedron Letters, 2017, vol. 58, # 46, p. 4352 - 4356]

41
[ 28443-50-7 ]
[ 127099-85-8 ]
[ 52112-68-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	With boron trifluoride diethyl etherate; In 1,4-dioxane; at 80℃;Inert atmosphere;	General procedure: To a solution of the corresponding 2-aminophenol (1equiv) and cyanoguanidine (3 equiv) in 1,4-dioxane (30 mL/g of 2-aminophenol)was added boron trifluoride diethyl etherate (3.0 equiv). The reaction was heated under argon atmosphere at 80C until completion (TLC monitoring, 5-16h). Then, the cooled reaction mixture was quenched with coldsaturated aqueous sodium hydrogen carbonate (100mL/g of 2-aminophenol) and extracted with ethyl acetate (3×100 mL). The combinedorganic layers were dried with anhydrous MgSO4 and evaporated.Depending on purity of the crude material, the residue was washed EtOAc,acetone or another organic solvent, or purified by silicagel flashchromatography (cyclohexane/EtOAc, 100/0 to 0/100, v/v) to afford the desiredproduct. All physical data of the knowncompounds were in agreement with those reported in the literature.

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 1642 - 1645

42
[ 352-23-8 ]
[ 28443-50-7 ]
ethyl 2-(6-chlorobenzo[d]oxazol-2-yl)acetate [ No CAS ]

Reference： [1]RSC Advances,2018,vol. 8,p. 16019 - 16023

43
[ 28443-50-7 ]
[ 128-04-1 ]
[ 22876-20-6 ]

Yield	Reaction Conditions	Operation in experiment
55%	With aluminum (III) chloride In water; N,N-dimethyl-formamide at 120℃;

Reference： [1]Liu, Xing; Zhang, Shi-Bo; Dong, Zhi-Bing [European Journal of Organic Chemistry, 2018, vol. 2018, # 39, p. 5406 - 5411]

44
[ 28443-50-7 ]
[ 1895-39-2 ]
6-chloro-3-(difluoromethyl)benzo[d]oxazole-2(3H)-thione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With sulfur; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium t-butanolate In N,N-dimethyl-formamide at 70℃; for 3h; Molecular sieve; Inert atmosphere;
78%	With sulfur; sodium t-butanolate In N,N-dimethyl-formamide at 70℃; for 3h; Molecular sieve;	2 Example 2 Place one PTFE magnet in a 25 mL reaction tube and add 0.4 mmol of 2-amino-5-chlorophenol.2 mmol S8,2 mmol of sodium difluorochloroacetate,1.6 mmol sodium tert-butoxide,60 mg molecular sieve and 6 mL N,N-dimethylformamide,After stirring for 3 h in a 70 ° C closed system,Extract three times with ethyl acetate.Combine the organic phase,Wash with saturated sodium chloride solution,After drying over anhydrous magnesium sulfate,The organic solvent was removed by rotary evaporation; the crude product was eluted with n-pentane and ethyl acetate.Agent,2-Mercapto-3-difluoromethyl-6-chloro-benzoxazole (yield 78%) was obtained by silica gel column chromatography.

Reference： [1]Li, Zhengyu; Dong, Jingnan; Yuan, Zihang; Yang, Ding-Yah; Weng, Zhiqiang [Organic Letters, 2018, vol. 20, # 20, p. 6407 - 6410]
[2]Current Patent Assignee: FUZHOU UNIVERSITY - CN108997243, 2018, A Location in patent: Page/Page column 7

45
[ 36818-07-2 ]
[ 28443-50-7 ]
C₁₅H₈ClN₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In diphenylether for 2h; Reflux;	4.1.2. General procedure for synthesis of 4-6 and 13 General procedure: Compound 2 (2.18 g, 10 mmol) and benzene-1,2-diamine (1.30 g,12 mmol) in Ph2O (10 mL) was heated to reflux for 2 h until thereaction completed (monitored by TLC). Then the mixture wascooled, filtered, and the solid was washed with petroleum ether(15mL x 3) to give 2.28 g of grey solid 4, which was used in nextstep without further purification. Compounds 5-6 and 13 weresynthesized followed the same procedure.

Reference： [1]Liu, Qing-Qing; Lu, Ke; Zhu, Hai-Miao; Kong, Shi-Lin; Yuan, Jing-Mei; Zhang, Guo-Hai; Chen, Nan-Ying; Gu, Chen-Xi; Pan, Cheng-Xue; Mo, Dong-Liang; Su, Gui-Fa [European Journal of Medicinal Chemistry, 2019, vol. 165, p. 293 - 308]

46
[ 557-21-1 ]
[ 28443-50-7 ]
[ 52112-68-2 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 1268 - 1272

47
[ 52200-48-3 ]
[ 15226-74-1 ]
[ 28443-50-7 ]
9-chlorobenzo[b]pyrido[3,2-f ][1,4]oxazepin-5(6H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 135℃; for 12h;Sealed tube; Inert atmosphere;	General procedure: Method A: A sealed tube equipped with a magnetic stir bar was charged with the corresponding 3-bromo-2-fluoropyridine (1 mmol), amino phenol (1 mmol), Pd(OAc)2 (5 mol%), xantphos (5 mol%) and DMAP (2.5 mmol). The tube was purged with argon. Then DMF (10V) was added followed by the addition of Co2(CO)8 (0.25 mmol). The tube was closed with seal plug instantly. The reaction tube was placed in a preheated oil bath at 120 0C for 8 h. On completion, the reaction mixture was cooled to room temperature, added water and ethyl acetate (1:1). Precipitated solid was filtered through a Celite bed. The bed was washed thoroughly with ethyl acetate. Organic layer was separated. Aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure and purified by flash column chromatography on silica gel (230-400 mesh) with ethyl acetate and petroleum ether as eluent to afford the corresponding pyridobenzoxazepinone. Method B: A sealed tube equipped with a magnetic stir bar was charged with the corresponding <strong>[52200-48-3]3-bromo-2-chloropyridine</strong> (1 mmol), amino phenol (1 mmol), Pd(OAc)2 (5 mol%), xantphos (5 mol%) and DBU (2.5 mmol). The tube was purged with argon. Then DMF (10 V) was added followed by the addition of Co2(CO)8 (0.25 mmol). The tube was closed with seal plug instantly. The reaction tube was placed in a pre heated oil bath at 135 0C for 12 h. On completion, the reaction mixture was cooled to room temperature, added water and ethyl acetate (1:1). Precipitated solid was filtered through a Celite bed. The bed was washed thoroughly with ethyl acetate. Organic layer was separated. Aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure and purified by flash column chromatography on silica gel (230-400 mesh) with ethyl acetate and petroleum ether as eluent to afford the corresponding pyridobenzoxazepinone.

Reference： [1]Synthetic Communications,2020,vol. 50,p. 348 - 360

48
[ 50-00-0 ]
[ 28443-50-7 ]
[ 92-44-4 ]
6,6'-(4,9-dihydronaphtho[1,2-e:4,3-e']bis([1,3]oxazine)-3,10(2H,11H)-diyl)bis(3-chlorophenol) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With <i>L</i>-proline In neat (no solvent) at 80℃; for 0.4h;	General procedure for the synthesis of 3,10-diphenyl-2,3,4,9,10,11-hexahydronaphtho[1,2-e:4,3-e']bis[1,3]oxazine (4a) General procedure: A mixture of 2,3-dihydroxynaphthalene (1a, 1 mmol), formaldehyde (2, 4 mmol) and aniline (3a, 2 mmol) and 10 mol % L-proline was added, and the mixture was stirred at 80 °C under solvent-free conditions. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled to room temperature, water was added, and the mixture was stirred for 5 min. The solid obtained was removed by filtration and recrystallized from ethanol to afford the pure white product 4a (92%) yield. Compounds (4a-4w) were also synthesized by adopting this procedure.

Reference： [1]Jadhav, Amol Maruti; Balwe, Sandip Gangadhar; Cho, Byung Gwon; Lim, Kwon Taek; Jeong, Yeon Tae [Synthetic Communications, 2020, vol. 50, # 5, p. 742 - 751]

49
[ 5731-10-2 ]
[ 28443-50-7 ]
6-chloro-2-(4'-fluoro-[1,1'-biphenyl]-4-yl)benzo[d]oxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With PPA at 150℃; for 0.5h;	9 EXAMPLE 9. 6-CHLORO-2-(4'-FLUORO-[l, r-BIPHENYL]-4-YL)BENZO[D]OXAZOLE (Cmp. 9) The mixture of compound 9A (6.97 mmol) and compound IB (1.38 g, 6.97 mmol,) in PPA (10.0 mL) are heated to 150°C and stirred for 0.5h. The reaction mixture is slowly added to saturated sodium bicarbonate solution (200 mL), then extracted with EtOAc (200 mL), the organic layer is washed with brine (200 mL), dried over Na2SC>4, filtered and concentrated to afford the crude product. The crude product is purified by column chromatography (Si02, Petroleum ether/Ethyl acetate=10: 1 to 5: 1) to afford the purified product, Compound 9

Reference： [1]Current Patent Assignee: MONTEFIORE MEDICAL CENTER - WO2020/77024, 2020, A1 Location in patent: Paragraph 0115; 0116

50
[ 28443-50-7 ]
[ 488-17-5 ]
C₁₃H₈ClNO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With cobalt(II) sulfate; 3,4,5-trihydroxybenzoic acid; oxygen; sodium carbonate In water at 15℃; for 40h;	Synthesis of 2-hydroxyphenoloxazin-3-one: General procedure: In a 150 mL reactor, put 2.18 g o-aminophenol, 1.88 g catechol, 2.2 mg gallic acid, 0.3 g iron sulfate, 0.25 g copper carbonate, 80 mg NaOH and 60 mL water. Heat to 40°C with stirring, add oxygen, keep the pressure in the reactor at 0.3 MPa, stop the reaction after 20 hours of reaction, cool to room temperature, extract with 3 × 15 mL of ethyl acetate, combine ethyl acetate layers, remove by rotary evaporation Ethyl acetate, the remaining solid was recrystallized with isopropanol, suction filtered, and dried to obtain 3.6g of black solid. The structure of the product was determined to be 2-hydroxyphenoloxazin-3-one by NMR (see attached picture), MS, etc. , The yield was 87%, and the purity of the product analyzed by liquid chromatography was 98%.

Reference： [1]Current Patent Assignee: ZHENGZHOU UNIVERSITY - CN111233781, 2020, A Location in patent: Paragraph 0025; 0028

51
[ 28443-50-7 ]
[ 56-81-5 ]
[ 5622-06-0 ]

Yield	Reaction Conditions	Operation in experiment
24%	With sulfuric acid In nitrobenzene-d5 at 140℃; for 6h; Sealed tube;	3.1 Step 1) Preparation of 6-chloroquinoline-8-phenol (3b) At room temperature, add 2-amino-5-chlorophenol (3a) (1.0g, 6.9mmol), glycerin (2.6mL, 34.8mmol), nitrobenzene (5.0mL) and concentrated sulfuric acid (1.0mL) to the sealed tube in sequence. , 18.8mmol).Seal the tube, stir the reaction solution at 140 for 6h, cool to room temperature, add ice water (20.0mL), then slowly adjust the pH of the water phase to about 8-9 with ammonia water, use dichloromethane (10.0mL x 3 ) Extract, combine the organic phases, dry with anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure.The residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=10/1) to obtain 6-chloroquinoline-8-phenol (3b) (300 mg, yield 24%).

Reference： [1]Current Patent Assignee: JIANGSU YAHONG MEDITECH; JIANGSU YAHONG MEDICINE SCIENCE TECH; SHANGHAI YAHONG PHARMACEUTICAL TECH; SHANGHAI YAHONG MEDITECH - CN111960998, 2020, A Location in patent: Paragraph 0251-0254

52
[ 28443-50-7 ]
[ 488-17-5 ]
7-chloro-2-hydroxy-4-methyl-3H-phenoxazin-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With 3,4,5-trihydroxybenzoic acid; oxygen; manganese(II) acetate; sodium hydroxide In water at 25℃; for 0.566667h; Sonication; Autoclave; Green chemistry; regioselective reaction;

Reference： [1]Li, Wenhao; Duan, Wenxue; Tang, Qingxuan; Li, Zhan-Ting; Yang, Guanyu [Green Chemistry, 2021, vol. 23, # 3, p. 1136 - 1139]

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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
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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

[ CAS No. 28443-50-7 ] {[proInfo.proName]}

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[ 28443-50-7 ] Synthesis Path-Upstream 1~22

[ 28443-50-7 ] Synthesis Path-Downstream 1~52

Related Functional Groups of [ 28443-50-7 ]

Aryls

Chlorides

Amines

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[ 28443-50-7 ]