[ CAS No. 2786-51-8 ] {[proInfo.proName]}

Name: 2786-51-8|5-Chlorobenzo[d]thiazole|95%
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Quality Control of [ 2786-51-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 2786-51-8 ]

Product Details of [ 2786-51-8 ]

CAS No. :	2786-51-8	MDL No. :	MFCD00227392
Formula :	C₇H₄ClNS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YTSFYTDPSSFCLU-UHFFFAOYSA-N
M.W :	169.63	Pubchem ID :	14388566
Synonyms :

Calculated chemistry of [ 2786-51-8 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	44.63
TPSA :	41.13 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 :	No
Log Kp (skin permeation) :	-5.46 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.06
Log Po/w (XLOGP3) :	2.64
Log Po/w (WLOGP) :	2.95
Log Po/w (MLOGP) :	2.11
Log Po/w (SILICOS-IT) :	3.83
Consensus Log Po/w :	2.72

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.22
Solubility :	0.102 mg/ml ; 0.000601 mol/l
Class :	Soluble
Log S (Ali) :	-3.15
Solubility :	0.119 mg/ml ; 0.000701 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.58
Solubility :	0.0447 mg/ml ; 0.000264 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.79

Safety of [ 2786-51-8 ]

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

Application In Synthesis of [ 2786-51-8 ]

* 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 [ 2786-51-8 ]
Downstream synthetic route of [ 2786-51-8 ]

[ 2786-51-8 ] Synthesis Path-Upstream 1~8

1
[ 2941-48-2 ]
[ 2786-51-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; palladium diacetate; triphenylphosphine In tetrahydrofuran at 25℃; for 1.5 h; Inert atmosphere	General procedure: Pd(OAc)₂-PPh₃, Pd₂(dba)₃-tbpf, Pd₂(dba)₃-DavePhos Pd₂(dba)₃-P(t-Bu)₃ Pd₂(dba)₃-XantPhos and Pd(OAc)₂-XPhos. Anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes, then Pd(OAc)₂ (7.2 mg, 0.033 mmol, 5 molpercent) and PPh₃ (17.7 mg, 1.132 mmol, 20 molpercent) were added and the resulting mixture stirred at room temperature for 30 min. The halogenated heterocycle (0.66 mmol), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH₄ (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature or heated at 65 °C under argon for the proper time. The residue was taken up in brine and extracted with ethyl acetate. The organic phase was separated, dried, the solvent was evaporated and the residue was purified by flash chromatography (mixtures of petroleum ether and ethyl acetate) to give pure hydrodehalogenated heterocycles

Reference： [1] Journal of Molecular Catalysis A: Chemical, 2014, vol. 393, p. 191 - 209

2
[ 124-38-9 ]
[ 1004-00-8 ]
[ 2786-51-8 ]

Reference： [1] RSC Advances, 2014, vol. 4, # 100, p. 56957 - 56960
[2] ACS Catalysis, 2015, vol. 5, # 11, p. 6648 - 6652

3
[ 1004-00-8 ]
[ 2786-51-8 ]

Reference： [1] Journal of the American Chemical Society, 1931, vol. 53, p. 2654,2656

4
[ 2565-30-2 ]
[ 615-48-5 ]
[ 2786-51-8 ]

Reference： [1] Journal of the American Chemical Society, 1931, vol. 53, p. 2654,2656

5
[ 5331-91-9 ]
[ 2786-51-8 ]

Reference： [1] Gazzetta Chimica Italiana, 1965, vol. 95, p. 499 - 506

6
[ 68-12-2 ]
[ 1004-00-8 ]
[ 2786-51-8 ]

Reference： [1] New Journal of Chemistry, 2016, vol. 40, # 10, p. 8282 - 8287

7
[ 5331-91-9 ]
[ 2786-51-8 ]

Reference： [1] Patent: US2509453, 1947, ,
[2] Patent: US2509454, 1947, ,

8
[ 64-18-6 ]
[ 89-61-2 ]
[ 2786-51-8 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1964, p. 2857 - 2867

[ 2786-51-8 ] Synthesis Path-Downstream 1~88

1
5-chloro-2,3-dihydro-benzothiazole [ No CAS ]
[ 2786-51-8 ]

Reference： [1]Journal of the American Chemical Society,1931,vol. 53,p. 2654,2656

2
[ 5331-91-9 ]
[ 2786-51-8 ]

Reference： [1]Patent: US2509453,1947,

3
[ 2565-30-2 ]
[ 615-48-5 ]
[ 2786-51-8 ]

Reference： [1]Journal of the American Chemical Society,1931,vol. 53,p. 2654,2656

4
[ 5331-91-9 ]
[ 2786-51-8 ]

Reference： [1]Gazzetta Chimica Italiana,1965,vol. 95,p. 499 - 506

5
[ 64-18-6 ]
[ 89-61-2 ]
[ 2786-51-8 ]

Reference： [1]Bulletin de la Societe Chimique de France,1964,p. 2857 - 2867

6
[ 2786-51-8 ]
[ 118-92-3 ]
[ 149474-18-0 ]

Reference： [1]Tetrahedron Letters,1991,vol. 32,p. 39 - 42

7
[ 2786-51-8 ]
5H-1-Thia-3,5-diaza-cyclopenta[b]anthracen-10-one [ No CAS ]

Reference： [1]Tetrahedron Letters,1991,vol. 32,p. 39 - 42

8
[ 1004-00-8 ]
[ 2786-51-8 ]

Reference： [1]Journal of the American Chemical Society,1931,vol. 53,p. 2654,2656

9
[ 2786-51-8 ]
[ 2896-45-9 ]

Reference： [1]Bulletin de la Societe Chimique de France,1964,p. 2857 - 2867

10
[ 2786-51-8 ]
[ 2786-29-0 ]

Reference： [1]Bulletin de la Societe Chimique de France,1964,p. 2857 - 2867

11
[ 2786-51-8 ]
[ 2786-54-1 ]

Reference： [1]Bulletin de la Societe Chimique de France,1964,p. 2857 - 2867

12
[ 2786-51-8 ]
[ 2786-55-2 ]

Reference： [1]Bulletin de la Societe Chimique de France,1964,p. 2857 - 2867

13
[ 2786-51-8 ]
[ 5663-96-7 ]
[ 1204299-71-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2009,vol. 48,p. 853 - 857

14
[ 2786-51-8 ]
[ 637-44-5 ]
[ 1204299-66-0 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2009,vol. 48,p. 853 - 857

15
[ 2786-51-8 ]
[ 3479-10-5 ]

Reference： [1]Journal of Molecular Catalysis A: Chemical,2010,vol. 328,p. 99 - 107
[2]Synthetic Communications,2011,vol. 41,p. 2343 - 2349

16
[ 2786-51-8 ]
[ 939-18-4 ]
[ 1227401-32-2 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 2692 - 2698

17
[ 1006-68-4 ]
[ 2786-51-8 ]
[ 1388625-42-0 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 3854 - 3857

18
[ 2786-51-8 ]
[ 591-50-4 ]
5-chloro-2-(phenylthio)benzo[d]thiazole [ No CAS ]

Reference： [1]Synthesis,2013,vol. 45,p. 1247 - 1255

19
[ 2786-51-8 ]
[ 615-41-8 ]
[ 1443355-98-3 ]

Reference： [1]Synthesis,2013,vol. 45,p. 1247 - 1255

20
[ 2786-51-8 ]
[ 625-99-0 ]
[ 1443356-09-9 ]

Reference： [1]Synthesis,2013,vol. 45,p. 1247 - 1255

21
[ 2786-51-8 ]
[ 352-34-1 ]
[ 1443356-13-5 ]

Reference： [1]Synthesis,2013,vol. 45,p. 1247 - 1255

22
[ 2786-51-8 ]
[ 395-35-7 ]
5-chloro-2-(4-(trifluoromethyl)phenyl)benzothiazole [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 5990 - 5993

23
[ 2786-51-8 ]
[ 104-87-0 ]
5-chloro-2-(4-methylphenyl)benzothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With tert.-butylhydroperoxide; copper dichloride; In water; at 80℃; for 24.5h;Inert atmosphere; Schlenk technique;	General procedure: A 25 mL reaction vessel was charged with benzothiazole 1 (1.86 mmol, 1.1 equiv), aldehyde 2 (1.69 mmol), CuCl2 (0.51mmol, 0.3 equiv), and tert-butylhydroperoxide (2.36 mmol, 1.4 equiv, 70% aqueous solution) under nitrogen. The reactionmixture was stirred in an ice bath for 30 min, and then stirred at 80C for 24 h. After cooling to room temperature, the mixture was purified by column chromatography using silica gel (petroleum ether/ethyl acetate) to afford the products 3.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 1806 - 1809

24
[ 2941-48-2 ]
[ 2786-51-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; palladium diacetate; triphenylphosphine; In tetrahydrofuran; at 25℃; for 1.5h;Inert atmosphere;	General procedure: Pd(OAc)2-PPh3, Pd2(dba)3-tbpf, Pd2(dba)3-DavePhos Pd2(dba)3-P(t-Bu)3 Pd2(dba)3-XantPhos and Pd(OAc)2-XPhos. Anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes, then Pd(OAc)2 (7.2 mg, 0.033 mmol, 5 mol%) and PPh3 (17.7 mg, 1.132 mmol, 20 mol%) were added and the resulting mixture stirred at room temperature for 30 min. The halogenated heterocycle (0.66 mmol), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature or heated at 65 C under argon for the proper time. The residue was taken up in brine and extracted with ethyl acetate. The organic phase was separated, dried, the solvent was evaporated and the residue was purified by flash chromatography (mixtures of petroleum ether and ethyl acetate) to give pure hydrodehalogenated heterocycles

Reference： [1]Journal of Molecular Catalysis A: Chemical,2014,vol. 393,p. 191 - 209

25
[ 2786-51-8 ]
[ 98-86-2 ]
[ 32729-67-2 ]

Reference： [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 2445 - 2452

26
[ 2786-51-8 ]
[ 99-91-2 ]
(5-chlorobenzothiazol-2-yl)(4-chlorophenyl)methanone [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 2445 - 2452

27
[ 2786-51-8 ]
[ 5736-89-0 ]
(4-butoxyphenyl)(5-chlorobenzothiazol-2-yl)methanone [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 2445 - 2452

28
[ 124-38-9 ]
[ 1004-00-8 ]
[ 2786-51-8 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 56957 - 56960
[2]ACS Catalysis,2015,vol. 5,p. 6648 - 6652

29
[ 2786-51-8 ]
[ 4559-70-0 ]
(5-chlorobenzo[d]thiazol-2-yl)diphenylphosphine oxide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 5433 - 5439
[2]Organic Letters,2016,vol. 18,p. 452 - 455
[3]Journal of Organic Chemistry,2016,vol. 81,p. 4682 - 4689
[4]Chemical Communications,2015,vol. 51,p. 3450 - 3453
[5]European Journal of Organic Chemistry,2017,vol. 2017,p. 1757 - 1759

30
[ 1008-89-5 ]
[ 2786-51-8 ]
5-chloro-2-(2-(pyridin-2-yl)phenyl)benzothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With dirhodium tetraacetate; copper(l) iodide; copper diacetate; triphenylphosphine; In N,N-dimethyl acetamide; at 160℃; for 9h;Inert atmosphere;	General procedure: Rh(OAc)2]2 (4.4 mg, 0.01 mmol), 2-phenylpyridine 1a (31 mg, 0.2 mmol), PPh3 (10.4 mg, 0.04 mmol), CuI (38.2 mg, 0.2 mmol), Cu(OAc)2 (108.6 mg, 0.6 mmol), N,N-dimethylacetamide (2.0 mL) were placed inside a 10 mL Schlenk tube equipped with a reflux condenser. Then, the temperature was risen to 160 C. Benzothiazole 2a (81 mg, 0.6 mmol) was separated into five portions and each portion was added within 1 h. After finishing addition, the solution was stirred under argon atmosphere at 160 C for another 4 h. After cooling to room temperature, the reaction mixture was quenched with ethyl acetate (15 mL) and washed with water (30 mL). The aqueous phase was extracted twice with EtOAc (3*10 mL), and the combined organic layer was dried over anhydrous Na2SO4. After evaporation of the solvents in vacuo, the crude product was purified by column chromatography on silica gel (petroleum ether/EtOAc=3/1) to give desire product Yield: 91%. Yellow oil. 1H NMR (600 MHz, CDCl3) delta 8.59 (d, J=4.5 Hz, 1H), 7.93 (dd, J=7.8, 1.5 Hz, 2H), 7.66-7.56 (m, 4H), 7.54 (m, 1H), 7.29 (dd, J=8.5, 1.9 Hz, 1H), 7.22 (m, 1H); 13C NMR (150 MHz, CDCl3) delta 169.8, 158.4, 154.2, 149.7, 141.5, 140.9, 136.4, 134.9, 132.6, 132.2, 130.9, 130.7, 129.0, 125.7, 125.1, 123.3, 122.6, 122.3; IR (KBr) nu=3060, 1590, 1494, 1457, 1428, 1393, 1314, 1255, 1099, 1037, 895, 782, 759, 729, 691 cm-1; HRMS: calcd for C18H11ClN2S: 322.0331, found: 322.0333.

Reference： [1]Tetrahedron,2014,vol. 70,p. 6474 - 6481

31
[ 2786-51-8 ]
[ 95-92-1 ]
C₁₁H₈ClNO₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%		[000282] To a solution of 5-chlorobenzo[ ]thiazole (500 mg, 2.95 mmol) in THF (20 mL) was added n-BuLi (1.42 ml, 3.54 mmol) at - 78 C under the protection of nitrogen. The mixture was stirred at - 78 C for 1 h, and then diethyl oxalate (1.08 g, 7.37 mmol) was added to the mixture and stirred for additional one hour at - 78 C. The reaction was quenched with sat. aqueous NH4C1. The organic phase was separated and washed with brine, dried over anhydrous Na2S04, and purified with column chromatography on silica gel (ethyl acetate in petroleum 20% v/v) to give Compound 6 A (200 mg, yield 25%) as a yellow solid. LCMS (m/z): 288 [M+18]+; 1H-NMR (CDC13, 400 MHz) major characteristic peaks: delta (ppm) 1.46 (t, J= 7.2 Hz, 3H), 4.54 (q, J= 7.2 Hz, 2H), 7.57 (dd, J= 2.0, 8.8 Hz, 1H), 7.95 (d, J = 8.8 Hz, 1H), 8.27 (d, J= 2.0 Hz, 1H).

Reference： [1]Patent: WO2015/42397,2015,A1 .Location in patent: Paragraph 000282

32
[ 2786-51-8 ]
ethyl 2-(5-chlorobenzo[d]thiazol-2-yl)-2,2-difluoroacetate [ No CAS ]

Reference： [1]Patent: WO2015/42397,2015,A1

33
[ 2786-51-8 ]
C₉H₄ClF₂NO₂S [ No CAS ]

Reference： [1]Patent: WO2015/42397,2015,A1

34
[ 2786-51-8 ]
2-(5-chlorobenzo[d]thiazol-2-yl)-N-((1R,2R)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl)-2,2-difluoroacetamide [ No CAS ]

Reference： [1]Patent: WO2015/42397,2015,A1

35
[ 2786-51-8 ]
4-bromo-3-iodo-toluene [ No CAS ]
2-chloro-7-methyl-10H-phenothiazine [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 4835 - 4839

36
[ 2786-51-8 ]
[ 583-55-1 ]
[ 92-39-7 ]

Reference： [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 4835 - 4839

37
[ 2786-51-8 ]
[ 31928-44-6 ]
[ 1730-45-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With N-methoxy-1H-pyrrole-2-carboxamide; copper(ll) sulfate pentahydrate; caesium carbonate; at 110℃; for 14h;Sealed tube;	The 170mg (1mmol) 5- chlorobenzothiazole, 317 (1mmol) 2- bromo-4-chloro-l-iodobenzene, 12.5mg (0.05mmol) CuSO4·5H2O14mg(0.1mmol)L1978mg(3mmol)Cs2CO3, 2gPEG-400, was added 10mL reaction tube, sealed, under the reaction conditions of 110 14h.After the reaction was stopped, extraction with ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure, column chromatography was purified by silica gel column to yield 201mg 2,8-dichloro-phenothiazine 75% yield.

Reference： [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 4835 - 4839
[2]Patent: CN104529938,2016,B .Location in patent: Paragraph 0084; 0085; 0086; 0087

38
[ 2786-51-8 ]
2-bromo-4-fluoro-1-iodobenzene [ No CAS ]
2-chloro-8-fluoro-10H-phenothiazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With N-methoxy-1H-pyrrole-2-carboxamide; copper(ll) sulfate pentahydrate; potassium carbonate; at 90℃; for 14h;Sealed tube;	The 170mg (1mmol) 5- chlorobenzothiazole, 241 (0.8mmol) 2- bromo-4-fluoro-1-iodobenzene, 12.5mg (0.05mmol) CuSO4·5H2O14mg(0.1mmol)L1690mg(5mmol)K2CO3, 2gPEG-400, was added 10mL reaction tube, sealed, under the reaction conditions of 90 14h.After the reaction was stopped, extraction with ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure, column chromatography was purified by silica gel column to give 2-chloro-8-fluoro-phenothiazine 222mg, yield 88%.

Reference： [1]Patent: CN104529938,2016,B .Location in patent: Paragraph 0088; 0089; 0090; 0091
[2]European Journal of Organic Chemistry,2015,vol. 2015,p. 4835 - 4839

39
[ 2786-51-8 ]
[ 79478-02-7 ]
(5-chlorobenzo[d]thiazol-2-yl)(4-(trifluoromethyl)phenyl)methanone [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 11065 - 11072

40
[ 2786-51-8 ]
[ 39687-95-1 ]
methyl 6-chlorobenzo[d]imidazo[2,1-b]thiazole-2-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 5336 - 5339

41
[ 2786-51-8 ]
[ 3859-41-4 ]
7-chloro-2,9-dihydro-1H-cyclopenta[b][1,4]benzothiazin-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium dihydrogenphosphate; In water; dimethyl sulfoxide; at 80℃; for 72h;	General procedure: A mixture of benzothiazole 1a (67.5 mg, 0.5 mmol), cyclohexane-1,3-dione 2b (112 mg, 1 mmol), KH2PO4 (136 mg, 1 mmol), DMSO (2 mL) and water (2 mL) were placed into a 15 mL flask under air. The reaction mixture was stirred in oil bath for 3 days at 80 C. The progress of the reaction was monitored by TLC. When the reaction was complete, it was neutralised with a saturated KHCO3 aqueous solution, and extracted with ethyl acetate (3 ×10 mL). The extract was washed with water (3 × 5 mL) and dried over anhydrous Na2SO4. After drying, it was concentrated under reduced pressure to give the crude product, which was further purified by silica-gel column chromatography to afford 2,3-dihydro-10H-phenothiazin-4 (1H)-ones 3b (93.2 mg, yield: 86%).

Reference： [1]Journal of Chemical Research,2015,vol. 39,p. 657 - 660

42
[ 2786-51-8 ]
[ 126-81-8 ]
8-chloro-2,2-dimethyl-2,3-dihydro-1H-phenothiazin-4(10H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium dihydrogenphosphate; In water; dimethyl sulfoxide; at 80℃; for 72h;	General procedure: A mixture of benzothiazole 1a (67.5 mg, 0.5 mmol), cyclohexane-1,3-dione 2b (112 mg, 1 mmol), KH2PO4 (136 mg, 1 mmol), DMSO (2 mL) and water (2 mL) were placed into a 15 mL flask under air. The reaction mixture was stirred in oil bath for 3 days at 80 C. The progress of the reaction was monitored by TLC. When the reaction was complete, it was neutralised with a saturated KHCO3 aqueous solution, and extracted with ethyl acetate (3 ×10 mL). The extract was washed with water (3 × 5 mL) and dried over anhydrous Na2SO4. After drying, it was concentrated under reduced pressure to give the crude product, which was further purified by silica-gel column chromatography to afford 2,3-dihydro-10H-phenothiazin-4 (1H)-ones 3b (93.2 mg, yield: 86%).

Reference： [1]Journal of Chemical Research,2015,vol. 39,p. 657 - 660

43
[ 2786-51-8 ]
[ 504-02-9 ]
8-chloro-2,3-dihydro-1H-phenothiazin-4(10H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium dihydrogenphosphate; In water; dimethyl sulfoxide; at 80℃; for 72h;	General procedure: A mixture of benzothiazole 1a (67.5 mg, 0.5 mmol), cyclohexane-1,3-dione 2b (112 mg, 1 mmol), KH2PO4 (136 mg, 1 mmol), DMSO (2 mL) and water (2 mL) were placed into a 15 mL flask under air. The reaction mixture was stirred in oil bath for 3 days at 80 C. The progress of the reaction was monitored by TLC. When the reaction was complete, it was neutralised with a saturated KHCO3 aqueous solution, and extracted with ethyl acetate (3 ×10 mL). The extract was washed with water (3 × 5 mL) and dried over anhydrous Na2SO4. After drying, it was concentrated under reduced pressure to give the crude product, which was further purified by silica-gel column chromatography to afford 2,3-dihydro-10H-phenothiazin-4 (1H)-ones 3b (93.2 mg, yield: 86%).

Reference： [1]Journal of Chemical Research,2015,vol. 39,p. 657 - 660

44
[ 2786-51-8 ]
[ 127-19-5 ]
N-((5-chlorobenzo[d]thiazol-2-yl)methyl)-N-methylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With dipotassium peroxodisulfate; eosin y; at 20℃; for 24h;Schlenk technique; Irradiation;	Weigh <strong>[2786-51-8]5-chlorobenzothiazole</strong> (0.5 mmol), K2S2O8 (2 eq.) and Eosin Y (2.0 mol%) in a 25 mL Schlenk reaction tube and addN,N-dimethylacetamide (6.612 g, 76 mmol), under air,The reaction was carried out under a 20 W LED white light, and the reaction was stirred at room temperature.Monitoring by TLC, the reaction was completed after 24 h, and the solvent was removed.The concentrate was separated by column chromatography (petroleum ether / ethyl acetate = 3: 1, V/V)A yellow oil is obtained, ie the derivative Ig. The yield was 84%.
78%	With dipotassium peroxodisulfate; eosin y; at 20℃; for 22h;Schlenk technique;	Weigh <strong>[2786-51-8]5-chlorobenzothiazole</strong> (0.5mmol, 85mg), K2S2O8 (1.5mmol, 0.41g) and Eosin Y (0.0075mmol, 4.9mg) in a 25mL Schlenk reaction tube,Then add N, N-dimethylacetamide (62.5mmol, 5.4g), put it under the LED white light of 15W power to react, stir the reaction at room temperature, monitor the progress of the reaction by TLC, the reaction ends after 22h, the reaction solution The solvent was removed by concentration, and the concentrated solution was separated by column chromatography (eluent: petroleum ether / ethyl acetate with a volume ratio of 3: 1) to obtain a yellow oil, that is, the derivative Ig. Yield was 78%.

Reference： [1]Patent: CN109053625,2018,A .Location in patent: Paragraph 0023
[2]Tetrahedron Letters,2019,vol. 60,p. 390 - 396
[3]Patent: CN110432282,2019,A .Location in patent: Paragraph 0050; 0051; 0052; 0053
[4]Journal of Organic Chemistry,2016,vol. 81,p. 3017 - 3022

45
[ 2786-51-8 ]
[ 60-12-8 ]
C₁₅H₁₃NOS [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 2444 - 2449

46
[ 2786-51-8 ]
[ 122-52-1 ]
[5-chloro-2-(diethoxyphosphoryl)benzothiazol-3-yl]phosphonic acid diethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With iodine; In acetonitrile; at 20℃; for 0.166667h;	5- chlorobenzothiazole 1m (85mg, 0.5mmol), I2(190mg, 0.75mmol), triethyl phosphite 2a (250mg, 1.5mmol), 2.0mL acetonitrile was added, reacted at room temperature for 10 minutes the reaction was stopped by column chromatography (silica gel column; eluent: petroleum ether / ethyl acetate = 1/1) to give the pure bis-phosphite adduct benzoxazole derivative 3ma.Product as a yellow liquid, yield 93%

Reference： [1]Patent: CN105541915,2016,A .Location in patent: Paragraph 0147; 0148; 0149; 0150; 0151
[2]Organic Letters,2017,vol. 19,p. 2242 - 2245

47
[ 2786-51-8 ]
[ 71838-16-9 ]
2-chloro-8-methylphenothiazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With N-methoxy-1H-pyrrole-2-carboxamide; copper(ll) sulfate pentahydrate; potassium carbonate; at 80℃; for 14h;Sealed tube;	The 170mg (1mmol) 5- chlorobenzothiazole, 534 (1.8mmol) 4- bromo-1-iodo-toluene, 12.5mg (0.05mmol) CuSO4·5H2O14mg(0.1mmol)L1690mg(5mmol)K2CO3, 2gPEG100, was added 10mL reaction tube, sealed, under the reaction condition of 80 14h.After the reaction was stopped, extraction with ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure, column chromatography was purified by silica gel column to give 2-chloro-8-methyl-phenothiazine piperazine 161mg, yield 65%.

Reference： [1]Patent: CN104529938,2016,B .Location in patent: Paragraph 0092; 0093; 0094; 0095

48
[ 68-12-2 ]
[ 1004-00-8 ]
[ 2786-51-8 ]

Reference： [1]New Journal of Chemistry,2016,vol. 40,p. 8282 - 8287

49
[ 2786-51-8 ]
1-methyl-2-oxo-1,2-dihydroquinolin-4-yl trifluoromethanesulfonate [ No CAS ]
C₁₇H₁₁ClN₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With copper(l) iodide; palladium(II) trifluoroacetate; potassium carbonate; tricyclohexylphosphine; In 5,5-dimethyl-1,3-cyclohexadiene; at 140℃; for 12h;Inert atmosphere;	General procedure: 1 mL Xylene was added into the flask charged with 0.25 mmol 4-quinolinonyl triflate, 0.75 mmol benzothiazole, 5 mol% Pd(TFA)2 (4.1 mg), 20 mol% PCy (14 mg), 0.25 mmol K2CO3, 10 mol% CuI (4.7 mg). The mixture was stirred at 140oC under Ar for 12 hours, then cooled down to room temperature, diluted with 20 mL ethyl acetate and washed with 10 mL H2O. The aqueous layer was extracted twice with ethyl acetate (5 mL) and the combined organic phase was dried over Na2SO4. After evaporation of the solvents the residue was purified by flash column chromatography (silica gel, PE/EtOAc) to afford the desired products 3 and 5.

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 5837 - 5840

50
[ 2786-51-8 ]
diethyl 6-chloro-3,4-dihydro-2H-benzo[b][1,4]thiazine-2,3-dicarboxylate [ No CAS ]