Name: 3507-26-4|2-Chloro-6-methylbenzo[d]thiazole|98%
Brand: Ambeed
SKU: A507307
Price: 23.0 USD
Availability: InStock
Rating: 96 (22 reviews)

1
[ 2536-91-6 ]
[ 3507-26-4 ]

Yield	Reaction Conditions	Operation in experiment
74%	With tert.-butylnitrite; copper dichloride; In acetonitrile; at 20℃;	t-Butyl nitrite (3.25 mL, 27.4 mmol) was added to a suspension of copper (II) chloride (2.95 g, 22.0 mmol) in CH3CN (31 mL). 6-Methyl-2- aminobenzothazole (3.0 g, 18 mmol) was added portionwise over ~30 min., and the reaction mixture was stirred at rt overnight. The reaction mixture was poured into 20% aqueous HCl (100 mL) and was extracted with EtOAc (3 x). The combined extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The material was purified by column chromatography (0 to10% EtOAc in Hexanes gradient), yielding 2.50 g (74%) of the title compound as a yellowish oil that solidified on standing. LC-MS: RT = 9.71 min., [M+H]+ = 184.0.

Reference： [1]Patent: WO2007/146066,2007,A2 .Location in patent: Page/Page column 93
[2]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 5275 - 5284
[3]Journal of Organic Chemistry,1947,vol. 12,p. 718,722
[4]Il Farmaco,1994,vol. 49,p. 153 - 166
[5]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4022 - 4025
[6]Chemistry and biodiversity,2011,vol. 8,p. 253 - 265
[7]Patent: US2230257,1937,

2
[ 3507-26-4 ]
[ 623-08-5 ]
[ 101281-22-5 ]

Reference： [1]Hunter et al. [Journal of the Chemical Society, 1958, p. 1561,1565]

3
[ 3507-26-4 ]
[ 118-92-3 ]
[ 22721-44-4 ]

Reference： [1]Bose; Pathak [Journal of the Indian Chemical Society, 1934, vol. 11, p. 463]

4
[ 3507-26-4 ]
[ 100-01-6 ]
6-methyl-N-(4-nitrophenyl)benzo[d]thiazol-2-amine [ No CAS ]

Reference： [1]Hunter; Jones [Journal of the Chemical Society, 1930, p. 2190,2209]

5
[ 3507-26-4 ]
[ 62-53-3 ]
[ 67058-58-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	at 100℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; Green chemistry;

Reference： [1]Cheng, Hua; Zhu, Yan-Qiu; Liu, Peng-Fei; Yang, Kai-Qiang; Yan, Jin; Sang, Wei; Tang, Xiao-Sheng; Zhang, Rui; Chen, Cheng [Journal of Organic Chemistry, 2021, vol. 86, # 15, p. 10288 - 10302]
[2]Hunter; Jones [Journal of the Chemical Society, 1930, p. 2190,2209] Hunter; Wali [Journal of the Chemical Society, 1937, p. 1513,1516] Suresh [Vikram, 1959, vol. 3, # 1, p. 16,18]

6
[ 3507-26-4 ]
[ 156-43-4 ]
[ 85063-56-5 ]

Reference： [1]Hunter; Jones [Journal of the Chemical Society, 1930, p. 2190,2209]

7
[ 3507-26-4 ]
[ 94-09-7 ]
4-(6-methyl-benzothiazol-2-ylamino)-benzoic acid ethyl ester [ No CAS ]

Reference： [1]Farooq; Hunter [Journal of the Indian Chemical Society, 1933, vol. 10, p. 563,568]

8
[ 3507-26-4 ]
[ 100-61-8 ]
[ 78072-95-4 ]

Reference： [1]Hunter; Wali [Journal of the Chemical Society, 1937, p. 1513,1516]

9
[ 3507-26-4 ]
[ 371-40-4 ]
[ 2369-32-6 ]

Reference： [1]Farooq; Hunter [Journal of the Indian Chemical Society, 1933, vol. 10, p. 465,469]

10
[ 3507-26-4 ]
[ 106-40-1 ]
[ 85063-54-3 ]

Reference： [1]Hunter; Jones [Journal of the Chemical Society, 1930, p. 2190,2209] Suresh [Vikram, 1959, vol. 3, # 1, p. 16,17]

11
[ 3507-26-4 ]
[ 540-37-4 ]
[ 791594-39-3 ]

Reference： [1]Farooq; Hunter [Recueil des Travaux Chimiques des Pays-Bas, 1935, vol. 54, p. 122,127]

13
[ 3507-26-4 ]
[ 2268-79-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogensulfide; ethanol

Reference： [1]Hasan; Hunter [Journal of the Chemical Society, 1936, p. 1672,1674]

14
[ 622-59-3 ]
[ 3507-26-4 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentachloride

Reference： [1]Hunter; Jones [Journal of the Chemical Society, 1930, p. 2190,2209]

15
[ 3507-26-4 ]
[ 1197-55-3 ]
[ 68194-97-8 ]

Yield	Reaction Conditions	Operation in experiment
	In acetic acid

Reference： [1]Sawhney,S.N. et al. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1978, vol. 16, p. 605 - 609]

16
[ 75-15-0 ]
[ 106-49-0 ]
[ 3507-26-4 ]

Yield	Reaction Conditions	Operation in experiment
	(i) KSCN, Br₂, (ii) aq. NaOH, (iii) /BRN= 1098293/, (iv) SO₂Cl₂; Multistep reaction;

Reference： [1]Bouanane,A. et al. [Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1976, vol. 283, p. 319 - 321]

17
[ 3507-26-4 ]
[ 106243-23-6 ]
2-[4-(1H-Imidazol-4-yl)-piperidin-1-yl]-6-methyl-benzothiazole [ No CAS ]

Reference： [1]Il Farmaco,1994,vol. 49,p. 153 - 166

18
[ 3507-26-4 ]
[ 95-53-4 ]
[ 78073-02-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 120 - 140℃; for 2h;

Reference： [1]Rashkes, Ya.V.; Ambartsumova, R.F.; Saprykina, V.A.; Rozhkova, N.K. [Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, p. 529 - 536][Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 3, p. 614 - 622]

Yield	Reaction Conditions	Operation in experiment
	Rk.mit NaOMe/MeOH (13-35grad) zu 2-Methoxy-6-methylbenzthiazol: Kinetik;
	Rk.mit Piperidin: Kinetik;

Yield	Reaction Conditions	Operation in experiment
	aus 2-Amino-6-methylbenzthiazol ueber das Diazoniumsalz;
	2-Amino-6-methylbenzthiazol: 1) Diazotierung 2) Cu2Cl2/wss.HCl;

21
[ 874483-75-7 ]
[ 622-59-3 ]
[ 3507-26-4 ]

Yield	Reaction Conditions	Operation in experiment
	at 170℃;

Reference： [1]Hunter; Jones [Journal of the Chemical Society, 1930, p. 2190,2209]

22
[ 3507-26-4 ]
[ 110-70-3 ]
C₂₀H₂₂N₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With potassium carbonate In isopropyl alcohol at 85℃;

Reference： [1]Byeon, Seong Rim; Jin, Yun Jung; Lim, Soo Jeong; Lee, Ji Hoon; Yoo, Kyung Ho; Shin, Kye Jung; Oh, Seung Jun; Kim, Dong Jin [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 14, p. 4022 - 4025]

23
[ 3507-26-4 ]
[ 107-15-3 ]
C₁₈H₁₈N₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With potassium carbonate In isopropyl alcohol at 85℃;

Reference： [1]Byeon, Seong Rim; Jin, Yun Jung; Lim, Soo Jeong; Lee, Ji Hoon; Yoo, Kyung Ho; Shin, Kye Jung; Oh, Seung Jun; Kim, Dong Jin [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 14, p. 4022 - 4025]

24
[ 20174-69-0 ]
[ 3507-26-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With thionyl chloride at 50℃; for 2h;

Reference： [1]Byeon, Seong Rim; Jin, Yun Jung; Lim, Soo Jeong; Lee, Ji Hoon; Yoo, Kyung Ho; Shin, Kye Jung; Oh, Seung Jun; Kim, Dong Jin [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 14, p. 4022 - 4025]

25
[ 3507-26-4 ]
[ 104-63-2 ]
[ 948588-53-2 ]

Reference： [1]Fujieda, Hiroki; Usui, Shinya; Suzuki, Takayoshi; Nakagawa, Hidehiko; Ogura, Michitaka; Makishima, Makoto; Miyata, Naoki [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 15, p. 4351 - 4357]

26
[ 3507-26-4 ]
[ 948588-55-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: DEAD; PPh₃ / tetrahydrofuran / 0 - 20 °C

Reference： [1]Fujieda, Hiroki; Usui, Shinya; Suzuki, Takayoshi; Nakagawa, Hidehiko; Ogura, Michitaka; Makishima, Makoto; Miyata, Naoki [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 15, p. 4351 - 4357]

27
[ 3507-26-4 ]
C₂₆H₂₆N₂O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: DEAD; PPh₃ / tetrahydrofuran / 0 - 20 °C 2: aq. NaOH / ethanol; tetrahydrofuran / 20 °C

Reference： [1]Fujieda, Hiroki; Usui, Shinya; Suzuki, Takayoshi; Nakagawa, Hidehiko; Ogura, Michitaka; Makishima, Makoto; Miyata, Naoki [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 15, p. 4351 - 4357]

28
[ 106-49-0 ]
[ 3507-26-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 32 percent / Br₂; AcOH / 1 h / cooling 2: 85 percent / NH₂NH₂H₂O; NH₂NH₂H₂SO₄ / ethane-1,2-diol / 2 h / 120 °C 3: 93 percent / SOCl₂ / 2 h / 50 °C

Reference： [1]Byeon, Seong Rim; Jin, Yun Jung; Lim, Soo Jeong; Lee, Ji Hoon; Yoo, Kyung Ho; Shin, Kye Jung; Oh, Seung Jun; Kim, Dong Jin [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 14, p. 4022 - 4025]

29
[ 3507-26-4 ]
[ 78073-00-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 100 percent / 2 h / 120 - 140 °C 2: 25 percent / ethanol / 20 h / Heating

Reference： [1]Rashkes, Ya.V.; Ambartsumova, R.F.; Saprykina, V.A.; Rozhkova, N.K. [Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, p. 529 - 536][Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 3, p. 614 - 622]

30
[ 106-49-0 ]
[ 3507-26-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 63.1 percent / Br₂ / acetic acid / 12 h / Ambient temperature 2: 1.) NaNO₂, H₂SO₄, 2.) CuCl, conc. HCl / 1.) glacial CH₃COOH, 0 deg C, 2.) CH₃COOH, r.t., overnight; 80 deg C, 2 h

Reference： [1]Bordi; Mor; Morini; Plazzi; Silva; Vitali; Caretta [Il Farmaco, 1994, vol. 49, # 3, p. 153 - 166]

31
[ 3507-26-4 ]
[ 3507-35-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: ethanol; NaHS 2: methanol

Reference： [1]Hasan; Hunter [Journal of the Chemical Society, 1936, p. 1672,1674]

32
[ 3507-26-4 ]
[ 78072-95-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 2: ethanolic sodium ethylate

Reference： [1]Hunter; Wali [Journal of the Chemical Society, 1937, p. 1513,1516]

33
[ 3507-26-4 ]
[ 78072-99-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 2: Behandeln des Reaktionsgemisches mit wss. NH₃

Reference： [1]Hunter; Wali [Journal of the Chemical Society, 1937, p. 1513,1516]

34
[ 3507-26-4 ]
<i>N</i>-(6-methyl-benzothiazol-2-yl)-anthranilic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 2: ethanolic KOH

Reference： [1]Bose; Pathak [Journal of the Indian Chemical Society, 1934, vol. 11, p. 463]

35
[ 3507-26-4 ]
[ 501-94-0 ]
[ 1146693-19-7 ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate In acetonitrile at 80℃; for 16h;	146.A Example 146; 5-{2-[4-(4-Methyl-benzothiazol-2-yloxy)-phenyl]-ethyl}-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid amideStep A: 2-[4-(6-Methyl-benzothiazol-2-yloxy)-phenyl]-ethanol. To a solution of phenethyl alcohol (3.15 g, 22.86 mmol) and K2CO3 (5.26 g, 38.1 mmol) in CH3CN (35 mL) was added 2-chloro-6-methylbenzthiazole (3.5 g, 19.1 mmol). The reaction mixture was heated at 80° C. for 16 h. To the reaction mixture was added 1 N NaOH (30 mL) and isopropyl acetate (40 mL). The layers were separated and the aqueous layer was extracted with isopropyl acetate (2×30 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated. The resulting residue was purified by silica gel flash chromatography (20% to 90% EtOAc in hexanes) to afford the title compound (3.4 g, 63%). 1H NMR (500 MHz, CDCl3): 7.61 (d, J=8.3 Hz, 1H), 7.47 (s, 1H), 7.33-7.28 (m, 4H), 7.20 (d, J=8.3 Hz, 1H), 3.87 (br s, 2H), 2.90 (t, J=6.6 Hz, 2H), 2.44 (s, 3H).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2009/111794, 2009, A1 Location in patent: Page/Page column 47

36
[ 3507-26-4 ]
[ 1028854-15-0 ]
[ 1148033-14-0 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In isopropyl alcohol; toluene at 150℃; for 22h;	2.3 Step 3: Synthesis of [4-(6-Methyl-benzothiazol-2-yl)-[l,4]diazepan-l-yl]-(tetrahydro- pyran-4-yl)-methanone; To a solution of 0.25 g (0.451 mmol) of [l,4]diazepan-l-yl-(tetrahydro-pyran-4-yl)- methanone (three trifluoroacetic acid equivalents, prepared according to step 1-2, Method 2) in toluene-isopropanol (4:1, 5 mL) are added 82.8 mg (0.451 mmol) of 2-chloro-6-methyl-l,3- benzothiazole, followed by 0.392 mL (2.26 mmol) of N,N-diisopropylethylamine. The reaction mixture is heated in a sealed tube to 150 0C for 22 h. The reaction is cooled to room temperature, concentrated under reduced pressure and the residue dissolved in dichloromethane (5 mL). The organic layer is washed with water (5 mL), dried (Na2SO4), filtered and the filtrate is concentrated under reduced pressure. The crude product is purified by column chromatography (silica, eluent: ethyl acetate) to afford 90.5 mg of [4-(6-methyl- benzothiazol-2-yl)-[l,4]diazepan-l-yl]-(tetrahydro-pyran-4-yl)-methanone. ES MS m/z 360 (M+H).

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2009/55357, 2009, A1 Location in patent: Page/Page column 32-33

37
[ 3507-26-4 ]
[ 2268-79-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 5275 - 5284

38
[ 3507-26-4 ]
[ 60-23-1 ]
[ 1185844-26-1 ]

Yield	Reaction Conditions	Operation in experiment
16%	In tetrahydrofuran Heating; Inert atmosphere;

Reference： [1]Location in patent: experimental part Cressier, Damien; Prouillac, Caroline; Hernandez, Pierre; Amourette, Christine; Diserbo, Michel; Lion, Claude; Rima, Ghassoub [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 14, p. 5275 - 5284]

39
[ 3507-26-4 ]
[ 20174-69-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate In ethanol; water for 3h; Reflux;

Reference： [1]Location in patent: experimental part Stella, Alessandro; Segers, Kenneth; De Jonghe, Steven; Vanderhoydonck, Bart; Rozenski, Jef; Anne, Jozef; Herdewijn, Piet [Chemistry and biodiversity, 2011, vol. 8, # 2, p. 253 - 265]

40
[ 45644-21-1 ]
[ 3507-26-4 ]
[ 1334294-01-7 ]

Yield	Reaction Conditions	Operation in experiment
24%	Stage #1: 6-chloropyridin-2-amine With sodium hydride In tetrahydrofuran; mineral oil for 0.333333h; Inert atmosphere; Cooling with ice; Stage #2: 2-chloro-6-methylbenzo[d]thiazole In tetrahydrofuran; mineral oil at 20℃; Stage #3: With ammonium chloride In tetrahydrofuran; water; mineral oil	Intermediate 1W-(6-chloro-2-pyridinyl)-6-methyl-1 ,3-benzothiazol-2-amineUnder an atmosphere of nitrogen, an ice-cooled solution of 6-chloro-2-pyridinamine (300mg, 2.33mmol) in tetrahydrofuran (15ml_) was treated portionwise with sodium hydride (60% w/w in oil) (121 mg, 3.03mmol). After 20 minutes, the mixture was treated with 2-chloro-6-methyl-1 ,3-benzothiazole (471 mg, 2.57mmol) and allowed to stir and warm to ambient temperature overnight. The mixture was then cautiously treated with saturated aqueous ammonium chloride (20ml_) and dichloromethane (50ml_). The organic phase was collected, evaporated to dryness and the product was purified by chromatography on silica using a gradient elution from 0 to 100% ethyl acetate in cyclohexane to afford the title compound (155mg, 0.56mmol, 24% yield). LCMS (Method A): Rt 1 .33 minutes; m/z 276 (MH+)

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/110575, 2011, A1 Location in patent: Page/Page column 63

41
[ 45644-21-1 ]
[ 3507-26-4 ]
trans-4-({6-[(6-methyl-1,3-benzothiazol-2-yl)amino]-2-pyridinyl}amino)cyclohexanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / Inert atmosphere; Cooling with ice 1.2: 20 °C 2.1: ethylene glycol / 3 h / 220 °C / Sealed tube; Microwave irradiation

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/110575, 2011, A1

42
[ 3507-26-4 ]
[ 35303-76-5 ]
[ 1340598-19-7 ]

Yield	Reaction Conditions	Operation in experiment
9%	In (+/-)-2-pentanol; acetonitrile at 200℃; for 0.166667h; Microwave irradiation;	4 Example 4 : N-{2-[4-(Aminosulfonyl)phenyl]ethyl}-1 -(6-methyl-1 ,3-benzothiazol- 2-yl)-3-piperidinecarboxamide (E4)A mixture of 2-chloro-6-methyl-1 ,3-benzothiazole (commercially available) (25mg, 0.14mmol) and /V-{2-[4-(aminosulfonyl)phenyl]ethyl}-3-piperidinecarboxamide (for a method of preparation see, for example, Description 2) (43mg, 0.14mmol) in 2- pentanohacetonitrile (4:1 v/v, 2ml) was heated in the microwave at 200°C for 10 minutes on high absorbance. The solvent of the mixture was then removed in vacuo and the resulting residue was purified using the MDAP. Fractions containing product were combined and the solvent was removed in vacuo to give the title compound as a white solid which was left in the vacuum oven for 2h (9mg, 9%).1 H NMR (400 MHz, DMSO): δ 1 .48-1 .66 (2H, m), 1 .76 (1 H, d, J=12.8), 1.84 (1 H, d, J=12.8), 2.33 (3H, s), 2.40 (1 H, m), 2.80 (2H, t, J=7.0), 3.08-3.17 (2H, m), -3.30 (assumed 2H underneath the solvent signal, seen in 2D NMR), 3.87-4.01 (2H, m), 7.07 (1 H, d, J=8.0), 7.17 (2H, br), 7.33 (1 H, d, J=8.4), 7.40 (2H, d, J=8.0), 7.55 (1 H, s), 7.76 (2H, d, J=8.4), 8.09 (1 H, t, J=5.8).LCMS m/z (ES): 459, 460 [M+H]+.

Reference： [1]Current Patent Assignee: COVERGENCE PHARMACEUTICALS - WO2011/131975, 2011, A1 Location in patent: Page/Page column 32-33

43
[ 3507-26-4 ]
[ 960535-17-5 ]
[ 1609464-31-4 ]

Yield	Reaction Conditions	Operation in experiment
42%	With palladium diacetate; triphenylphosphine; sodium t-butanolate In toluene at 110℃;

Reference： [1]Clark, Roger B.; Lamppu, Diana; Libertine, Lyn; McDonough, Amy; Kumar, Anjali; LaRosa, Greg; Rush, Roger; Elbaum, Daniel [Journal of Medicinal Chemistry, 2014, vol. 57, # 10, p. 3966 - 3983]

44
[ 3507-26-4 ]
[ 250275-15-1 ]
5-(6-methylbenzothiazol-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5620 - 5636

45
[ 3507-26-4 ]
[ 57260-71-6 ]
tert-butyl 4-(6-methylbenzothiazol-2-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In N,N-dimethyl-formamide at 100℃;	General Procedure of Amine Synthesis (GP4) General procedure: GP4-1: A mixture of substituted2-chlorobenzothiazole (1.0eq), N-Bocpiperazine (1.05 eq) and Na2CO3 (1.2 eq) inDMF (10 volume) was heated up at 100 0C for hours, the process ofwhich was monitored by TLC. The mixture was diluted by EA and added by water.After extraction by EA (2 times), the collected organic layers were washed by10% citric acid, and then brine, dried over Na2SO4 andconcentrated to give crude product, which could be used directly withoutfurther purification.GP4-2: N-Bocprotected amine in DCM (5 volume) was added by TFA (2.5 volume). The mixturewas stirred at rt for four hours and monitored by TLC. After consumption ofstarting material, volatile solvent was removed under reduced pressure and theresidue was neutralized by saturated Na2CO3 solution toobtain the slurry, which was extracted by 10% methanol in DCM (3 times). Theorganic layers were collected, dried and concentrated to give the desired freeamine, for direct use for next step.GP4-3: Free amine (1.0 eq) suspendedin DCM (10 volume) was added by aldehyde (1.1 eq) under N2atmosphere. The mixture was stirred at rt 15 min. Then trimethylsilylazide (TMSN3, 1.1 eq) was added, and stirring was kept foranother 15 min, followed by addition of isonitrile (1.0 eq). The mixture wasstirred at for 12 h. After removal of solvent, the residue was purified bypreparative TLC (DCM/MeOH as eluent) to give the product, which could bere-purified by trituration with ether.

Reference： [1]Lv, Fengping; Li, Zhi-Fang; Hu, Wenhao; Wu, Xiaohua [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7661 - 7670]

46
[ 3507-26-4 ]
[ 1018498-61-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium carbonate / N,N-dimethyl-formamide / 100 °C 2: trifluoroacetic acid / dichloromethane / 4 h / 20 °C

Reference： [1]Lv, Fengping; Li, Zhi-Fang; Hu, Wenhao; Wu, Xiaohua [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7661 - 7670]

47
[ 3507-26-4 ]
6-methyl-2-(4-(1-(1-(thiophen-2-ylmethyl)-1H-tetrazol-5-yl)propyl)piperazin-1-yl)benzothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sodium carbonate / N,N-dimethyl-formamide / 100 °C 2.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C 3.1: dichloromethane / 0.25 h / 20 °C / Inert atmosphere 3.2: 0.25 h / Inert atmosphere 3.3: 12 h / Inert atmosphere

Reference： [1]Lv, Fengping; Li, Zhi-Fang; Hu, Wenhao; Wu, Xiaohua [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7661 - 7670]

48
[ 3507-26-4 ]
(2-ethylsulfonylphenyl)-piperazin-1-yl-methanone [ No CAS ]
(2-ethylsulfonylphenyl)-[4-(6-methyl-1,3-benzothiazol-2-yl)piperazin-1-yl]methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With sodium hydrogencarbonate In ethanol; water for 15h; Reflux;

Reference： [1]Migliore, Marco; Pontis, Silvia; Fuentes de Arriba, Angel Luis; Realini, Natalia; Torrente, Esther; Armirotti, Andrea; Romeo, Elisa; Di Martino, Simona; Russo, Debora; Pizzirani, Daniela; Summa, Maria; Lanfranco, Massimiliano; Ottonello, Giuliana; Busquet, Perrine; Jung, Kwang -Mook; Garcia-Guzman, Miguel; Heim, Roger; Scarpelli, Rita; Piomelli, Daniele [Angewandte Chemie - International Edition, 2016, vol. 55, # 37, p. 11193 - 11197][Angew. Chem., 2016, vol. 128, p. 11359 - 11363]

49
[ 3507-26-4 ]
[ 106-49-0 ]
[ 42238-71-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	In ethanol at 90℃; for 1h;	1 2-(4-methylanilino)-6-methylbenzothiazole (compound 1) 2-chloro-6-methylbenzothiazole (183 mg, available from Aldrich) and 4-methylaniline (107 mg, available from TCI ) Was added to 95% ethanol (30 mL) and the resulting mixture was heated at 90 °C for 1 hour, and the reaction was confirmed by thin layer chromatography during the experiment. Afterwards, the reaction was cooled to room temperature, followed by concentration under reduced pressure to remove the solvent, followed by 50 kL of dichloromethane Dichloromethane and 50 pL of water were added to the resulting residue And the extraction took 1 hour. Afterwards, the dichloromethane layer was collected and passed through silicon The gel column chromatography (n-hexane/ethyl acetate=3:1) was purified to give a title compound 1 as a white solid (218 mg, yield 86%).

Reference： [1]Current Patent Assignee: KAOHSIUNG MEDICAL UNIVERSITY - TWI543973, 2016, B Location in patent: Paragraph 0052

50
[ 3507-26-4 ]
[ 95-68-1 ]
2-(2,4-dimethylanilino)-6-methylbenzothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In ethanol at 90℃; for 13h;	2 2-(2,4-dimethylanilino)-6-methylbenzothiazole (compound 2) General procedure: 2-chloro-6-methylbenzothiazole (183 mg, available from Aldrich) and 4-methylaniline (107 mg, available from TCI ) Was added to 95% ethanol (30 mL) and the resulting mixture was heated at 90 °C for 1 hour, and the reaction was confirmed by thin layer chromatography during the experiment. Afterwards, the reaction was cooled to room temperature, followed by concentration under reduced pressure to remove the solvent, followed by 50 kL of dichloromethane Dichloromethane and 50 pL of water were added to the resulting residue And the extraction took 1 hour. Afterwards, the dichloromethane layer was collected and passed through silicon The gel column chromatography (n-hexane/ethyl acetate=3:1) was purified to give a title compound 1 as a white solid (218 mg, yield 86%). 2-(2,4-dimethylanilino)-6-methylbenzothiazole (Compound 2) was prepared substantially in accordance with the procedure described in Synthesis Example 1 above The difference is that the use of 121 mg 2,4-dimethylaniline (from TCI) was substituted for 4-methylaniline and heated at 90 °C for a period of time 13 hours. The title compound 2 was purified by silica gel column chromatography (n-hexane/ethyl acetate=3:1) with a pale yellow solid (214 mg, yield 80%).

Reference： [1]Current Patent Assignee: KAOHSIUNG MEDICAL UNIVERSITY - TWI543973, 2016, B Location in patent: Paragraph 0052; 0054

51
[ 3507-26-4 ]
[ 108-69-0 ]
2-(3,5-dimethylanilino)-6-methylbenzothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In ethanol at 90℃; for 10h;	3 2-(3,5-dimethylanilino)-6-methylbenzothiazole (compound 3) General procedure: 2-chloro-6-methylbenzothiazole (183 mg, available from Aldrich) and 4-methylaniline (107 mg, available from TCI ) Was added to 95% ethanol (30 mL) and the resulting mixture was heated at 90 °C for 1 hour, and the reaction was confirmed by thin layer chromatography during the experiment. Afterwards, the reaction was cooled to room temperature, followed by concentration under reduced pressure to remove the solvent, followed by 50 kL of dichloromethane Dichloromethane and 50 pL of water were added to the resulting residue And the extraction took 1 hour. Afterwards, the dichloromethane layer was collected and passed through silicon The gel column chromatography (n-hexane/ethyl acetate=3:1) was purified to give a title compound 1 as a white solid (218 mg, yield 86%). 2-(3,5-dimethylanilino)-6-methylbenzothiazole (Compound 3) was prepared substantially in accordance with the procedure described in Synthesis Example 1 above, except that 121 mg of 3,5-dimethylaniline (purchased from In Alfa Aesar) instead of 4-methylaniline, and heated at 90 °C for 10 hours. The title compound 3 was purified by silica gel column chromatography (n-hexane/ethyl acetate=3:1) with a tan solid (241 mg, yield 85%).

Reference： [1]Current Patent Assignee: KAOHSIUNG MEDICAL UNIVERSITY - TWI543973, 2016, B Location in patent: Paragraph 0052; 0056

52
[ 3507-26-4 ]
[ 104-94-9 ]
[ 85063-55-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	In ethanol at 90℃; for 8h;	4 2-(4-methoxyanilino)-6-methylbenzothiazole (compound 4) General procedure: 2-chloro-6-methylbenzothiazole (183 mg, available from Aldrich) and 4-methylaniline (107 mg, available from TCI ) Was added to 95% ethanol (30 mL) and the resulting mixture was heated at 90 °C for 1 hour, and the reaction was confirmed by thin layer chromatography during the experiment. Afterwards, the reaction was cooled to room temperature, followed by concentration under reduced pressure to remove the solvent, followed by 50 kL of dichloromethane Dichloromethane and 50 pL of water were added to the resulting residue And the extraction took 1 hour. Afterwards, the dichloromethane layer was collected and passed through silicon The gel column chromatography (n-hexane/ethyl acetate=3:1) was purified to give a title compound 1 as a white solid (218 mg, yield 86%). 2-(4-methoxyanilino)-6-methylbenzothiazole (Compound 4) was prepared substantially in accordance with the procedure described in Synthesis Example 1 above, except that 123 mg of 4-methoxyaniline (4-methoxyaniline) (available from TCI) to replace 4-methylaniline, and in Heating at 90 °C for 8 hours. The title compound 4 was purified by silica gel column chromatography (n-hexane/ethyl acetate=3:1) as a milky white solid (248 mg, yield 92%).

Reference： [1]Current Patent Assignee: KAOHSIUNG MEDICAL UNIVERSITY - TWI543973, 2016, B Location in patent: Paragraph 0052; 0058

53
[ 3507-26-4 ]
[ 20012-63-9 ]
2-(2-benzyloxyanilino)-6-methylbenzothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	In ethanol; at 90℃; for 16h;	General procedure: 2-chloro-6-methylbenzothiazole (183 mg, available from Aldrich) and 4-methylaniline (107 mg, available from TCI ) Was added to 95% ethanol (30 mL) and the resulting mixture was heated at 90 C for 1 hour, and the reaction was confirmed by thin layer chromatography during the experiment. Afterwards, the reaction was cooled to room temperature, followed by concentration under reduced pressure to remove the solvent, followed by 50 kL of dichloromethane Dichloromethane and 50 pL of water were added to the resulting residue And the extraction took 1 hour. Afterwards, the dichloromethane layer was collected and passed through silicon The gel column chromatography (n-hexane/ethyl acetate=3:1) was purified to give a title compound 1 as a white solid (218 mg, yield 86%). 2-(2-benzyloxyanilino)-6-methylbenzothiazole (compound 7) is substantially in accordance with the procedure described in Synthetic Example 1 above , Except that 199 mg of 2-benzyloxyaniline was used (2-benzyloxyaniline) (available from Acros) instead of 4-methylaniline and And heated at 90 C for 16 hours. The title compound 7 was obtained from Silica gel column chromatography (n-hexane/ethyl acetate=3:1) was purified with a brown Color liquid (218 mg, yield 63%).

Reference： [1]Patent: TWI543973,2016,B .Location in patent: Paragraph 0052; 0064

54
[ 3507-26-4 ]
[ 38762-41-3 ]
2-(4-bromo-2-chloroanilino)-6-methylbenzothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In ethanol; at 90℃; for 15h;	General procedure: 2-chloro-6-methylbenzothiazole (183 mg, available from Aldrich) and 4-methylaniline (107 mg, available from TCI ) Was added to 95% ethanol (30 mL) and the resulting mixture was heated at 90 C for 1 hour, and the reaction was confirmed by thin layer chromatography during the experiment. Afterwards, the reaction was cooled to room temperature, followed by concentration under reduced pressure to remove the solvent, followed by 50 kL of dichloromethane Dichloromethane and 50 pL of water were added to the resulting residue And the extraction took 1 hour. Afterwards, the dichloromethane layer was collected and passed through silicon The gel column chromatography (n-hexane/ethyl acetate=3:1) was purified to give a title compound 1 as a white solid (218 mg, yield 86%). 2-(4-bromo-2-chloroanilino)-6-methylbenzothiazole (Compound 11) was prepared substantially in accordance with the procedure described in Synthesis Example 1 above, except that: 206 mg of 4-bromo-2-chloroaniline (available from ACROS) was substituted for 4-methylaniline and heated at 90 C for 15 hours. The title compound 11 was purified by silica gel column chromatography (n-hexane/ethyl acetate=3:1) with a milky white solid (246 mg, yield 70%)

Reference： [1]Patent: TWI543973,2016,B .Location in patent: Paragraph 0052; 0072

55
[ 3507-26-4 ]
[ 99-09-2 ]
2-(3-nitroanilino)-6-methylbenzothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	In ethanol at 90℃; for 14h;	12 2-(3-nitroanilino)-6-methylbenzothiazole (compound 12) General procedure: 2-chloro-6-methylbenzothiazole (183 mg, available from Aldrich) and 4-methylaniline (107 mg, available from TCI ) Was added to 95% ethanol (30 mL) and the resulting mixture was heated at 90 °C for 1 hour, and the reaction was confirmed by thin layer chromatography during the experiment. Afterwards, the reaction was cooled to room temperature, followed by concentration under reduced pressure to remove the solvent, followed by 50 kL of dichloromethane Dichloromethane and 50 pL of water were added to the resulting residue And the extraction took 1 hour. Afterwards, the dichloromethane layer was collected and passed through silicon The gel column chromatography (n-hexane/ethyl acetate=3:1) was purified to give a title compound 1 as a white solid (218 mg, yield 86%). 2-(3-nitroanilino)-6-methylbenzothiazole (Compound 12) was prepared substantially in accordance with the procedure described in Synthesis Example 1 above, except that 138 mg of 3-nitroaniline (available from TCI) instead of 4-methylaniline, and heated at 90 °C for 14 hours. The title compound 12 was purified by silica gel column chromatography (n-hexane/ethyl acetate=3:1) with a yellow solid (208 mg, yield 73%).

Reference： [1]Current Patent Assignee: KAOHSIUNG MEDICAL UNIVERSITY - TWI543973, 2016, B Location in patent: Paragraph 0052; 0074

56
[ 3507-26-4 ]
None [ No CAS ]
None [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol Reflux;

Reference： [1]Current Patent Assignee: KAOHSIUNG MEDICAL UNIVERSITY - TWI543973, 2016, B Location in patent: Page/Page column 18

57
[ 3507-26-4 ]
4H-1‘-azaspiro[isoxazole-5,3‘-bicyclo[2.2.2]octan]-3-amine [ No CAS ]
(+/-)-N-(6-methylbenzo[d]thiazol-2-yl)-4H-1‘-azaspiro[isoxazole-5,3'-bicyclo[2.2.2]octan]-3-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%	With chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl-t-butyl ether adduct; sodium t-butanolate In 1,4-dioxane at 20℃; for 16h; Inert atmosphere;	14 Example 14: (+/-)-N-(6-methylbenzo [djthiazol-2-yl)-4H- 1 ‘-azaspiro[isoxazole-5 ,3 bicyclo[2.2.21 octanj-3-amine (rac-14) j00569j To a mixture of 2-chloro-6-methylbenzo[djthiazole (0.30 g, 1.6 mmol) and compound rac-A-2 (0.29 g, 1.6 mmol) in dioxane (10 mL) under nitrogen at room temperature was added sodium tert-butoxide (0.31 g, 3.2 mmol), dicyclohexyl-[2-(2,4,6-triisopropylphenyl)phenylj phosphane-[2-(2-aminoethyl)phenylj-chloro-palladium (0.12 g, 0.16 mmol). The reaction mixture was stirred at 20 °C for 16 hours, then filtered and concentrated in vacuo. The residue was purified by prep-HPLC [Instrument: Shimadzu pump LC-20A; Column: GEMiNI 200 x 50 mm, particle size: 10 .im; Mobile phase: 5 5-66.7% acetonitrile in H20 (add 0.5% NH3 H20, v/v)j to give compound rae- 14 (62 mg, 12% yield) as a white solid.

Reference： [1]Current Patent Assignee: SIO GENE THERAPIES INC - WO2017/69980, 2017, A1 Location in patent: Paragraph 00568; 00569

58
[ 583-68-6 ]
[ 3507-26-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide / 120 - 130 °C / Inert atmosphere 2.1: sulfuryl dichloride / 0.25 h / 20 - 25 °C / Inert atmosphere 2.2: 3 h / 20 - 25 °C / Inert atmosphere

Reference： [1]Wimmer, Laurin; Parmentier, Michael; Riss, Bernard; Kapferer, Tobias; Ye, Chao; Li, Lei; Kim, Hongyong; Li, Jialiang [Synthesis, 2018, vol. 50, # 10, p. 2027 - 2032]

59
[ 2268-79-3 ]
[ 3507-26-4 ]

Yield	Reaction Conditions	Operation in experiment
86%		General procedure: A mixture of the 2-mercaptobenzo[d]thiazole (>1 g, 1 equiv) and sul-furyl chloride (10 equiv) was stirred at 20-25 C for 15 min. Next, H 2 O(2 equiv) was added and the mixture was stirred at 20-25 C for anadditional 3 h. A sample was taken, quenched with MeCN/H 2 O (2:1)and analyzed by HPLC. After completion of the reaction, the mixturewas diluted with MeCN (5 volumes) and slowly quenched with H 2 O(20 volumes). The product precipitated from the aqueous solution.The solid was collected and washed with H 2 O. Drying under vacuumafforded the pure product. In the case of the liquid product 2-chloro-benzo[d]thiazole (13), the reaction mixture was extracted withEtOAc. The organic layer was then dried and concentrated to affordthe product as an oil.

Reference： [1]Synthesis,2018,vol. 50,p. 2027 - 2032

60
[ 3507-26-4 ]
[ 1146693-18-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 16 h / 80 °C 2: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 0 - 20 °C 3: potassium carbonate / tert-Amyl alcohol / 16 h / 80 °C

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2009/111794, 2009, A1

61
[ 3507-26-4 ]
C₁₇H₁₇NO₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 16 h / 80 °C 2: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2009/111794, 2009, A1

62
[ 3507-26-4 ]
[ 23046-68-6 ]
6-chloro-2-(6-methyl-1,3-benzothiazol-2-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium carbonate In N,N-dimethyl-formamide for 12h;	General procedure: Method A:41 To a round bottom flask was added tryptoline (21mg, 0.100mmol), 2-chlorobenzothiazole (31mg, 0.150mmol), K2CO3 (70mg, 0.500mmol) and DMF (2.0mL), and the reaction mixture was stirred for 12h at 110°C. After the reaction was then cooled to room temperature, ethyl acetate (10mL) and H2O (10mL) were added into the mixture, and the aqueous layer was extracted with 2×10mL ethyl acetate. The organic layer then was combined and washed with brine, and dried over Na2SO4. The solvents were removed under vacuum, and the residue was purified by flash chromatography on silica gel using ethyl acetate/hexane as eluent.

Reference： [1]Wang, Xinfeng; Chen, Jinsen; Wang, Wei; Jaunarajs, Anna; Wang, Xiang [Bioorganic and Medicinal Chemistry, 2019, vol. 27, # 21]

63
[ 3507-26-4 ]
[ 127-19-5 ]
N,N-dimethyl-2-(6-methylbenzo[d]thiazol-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃;

Reference： [1]Hu, Jinjin; Jiang, Min; Pan, Shulei; Wu, Binqiang; Xu, Ruigang; Zeng, Xiaofei; Zhong, Guofu [Journal of Organic Chemistry, 2019]

64
[ 3507-26-4 ]
(E)-N,N-dimethyl-2-(6-methylbenzo[d]thiazol-2-yl)-5-phenylpent-4-enamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium hexamethyldisilazane / tetrahydrofuran / -78 - 20 °C 2: diphenyl hydrogen phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water / 12 h / 100 °C

Reference： [1]Hu, Jinjin; Jiang, Min; Pan, Shulei; Wu, Binqiang; Xu, Ruigang; Zeng, Xiaofei; Zhong, Guofu [Journal of Organic Chemistry, 2019]

65
[ 3507-26-4 ]
N<SUP>1</SUP>-(6-chloro-1,2,3,4-tetrahydroacridin-9-yl)propane-1,3-diamine [ No CAS ]
N₁-(6-chloro-1,2,3,4-tetrahydroacridin-9-yl)-N₃-(6-methylbenzo[d]thiazol-2-yl)propane-1,3-diamine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%	Stage #1: 2-chloro-6-methylbenzo[d]thiazole; N<SUP>1</SUP>-(6-chloro-1,2,3,4-tetrahydroacridin-9-yl)propane-1,3-diamine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 110℃; for 2h; Inert atmosphere; Stage #2: With hydrogenchloride In methanol	5.2. General procedure for synthesis of tacrine - Benzothiazole hybrids(10a-10y) General procedure: Appropriate 2-chlorobenzothiazole (5-9, 1 eq) was placed in a flaskequipped with a stirring bar and septum. The flask was purged withargon and charged with DMF (5 mL). Thereafter, DIPEA (2 eq) wasadded into the mixture. Finally, appropriate α,ω-diaminotacrine derivative(4a-4u, 1 eq) were dissolved in a minimal amount of DMF andadded via the syringe. The resulting solution was then heated to 110 Cand stirred for 2 h. Subsequently, the mixture was cooled to roomtemperature and extracted with CH2Cl2 (3 × 100 mL) and water (100mL). Collected organic layers were dried over Na2SO4, filtered andevaporated to give crude product. The crude oil was purified by columnchromatography using ethyl acetate/MeOH/26% aqueous ammoniasolution (60/1/0.2) as eluent to yield a pure base. The pure base wasdissolved in MeOH and saturated with gaseous HCl. The solvent wasremoved and the residue was washed with acetonitrile to afford the finalproduct.

Reference： [1]Nepovimova, Eugenie; Svobodova, Lucie; Dolezal, Rafael; Hepnarova, Vendula; Junova, Lucie; Jun, Daniel; Korabecny, Jan; Kucera, Tomas; Gazova, Zuzana; Motykova, Katarina; Kubackova, Jana; Bednarikova, Zuzana; Janockova, Jana; Jesus, Catarina; Cortes, Luisa; Pina, Joao; Rostohar, Danijela; Serpa, Carlos; Soukup, Ondrej; Aitken, Laura; Hughes, Rebecca E.; Musilek, Kamil; Muckova, Lubica; Jost, Petr; Chvojkova, Marketa; Vales, Karel; Valis, Martin; Chrienova, Zofia; Chalupova, Katarina; Kuca, Kamil [Bioorganic Chemistry, 2021, vol. 107]

66
[ 3507-26-4 ]
potassium vinyltrifluoroborate [ No CAS ]
C₁₀H₉NS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; triethylamine In isopropyl alcohol for 16h; Reflux; Inert atmosphere;

Reference： [1]Zhang, Huihui; Wang, Min; Wu, Xinxin; Zhu, Chen [Angewandte Chemie - International Edition, 2021, vol. 60, # 7, p. 3714 - 3719][Angew. Chem., 2021, vol. 133, # 7, p. 3758 - 3763,6]

67
[ 3507-26-4 ]
C₁₈H₁₅NO₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; triethylamine / isopropyl alcohol / 16 h / Reflux; Inert atmosphere 2: copper(l) iodide; bathophenanthroline; sodium carbonate / dichloromethane / 72 h / 100 °C / Sealed tube; Inert atmosphere

Reference： [1]Zhang, Huihui; Wang, Min; Wu, Xinxin; Zhu, Chen [Angewandte Chemie - International Edition, 2021, vol. 60, # 7, p. 3714 - 3719][Angew. Chem., 2021, vol. 133, # 7, p. 3758 - 3763,6]

68
[ 3507-26-4 ]
[ 62-53-3 ]
6-methyl-N-(6-methylbenzo[d]thiazol-2-yl)-N-phenylbenzo[d]thiazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	at 100℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; Green chemistry;

Reference： [1]Cheng, Hua; Zhu, Yan-Qiu; Liu, Peng-Fei; Yang, Kai-Qiang; Yan, Jin; Sang, Wei; Tang, Xiao-Sheng; Zhang, Rui; Chen, Cheng [Journal of Organic Chemistry, 2021, vol. 86, # 15, p. 10288 - 10302]

69
[ 3507-26-4 ]
C₂₂H₁₉NOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: caesium carbonate / acetonitrile / 12 h / 60 °C / Inert atmosphere 2.1: hydrogenchloride / water / 1 h 2.2: 0.25 h / Inert atmosphere 3.1: (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; ascorbic acid / acetonitrile / 26 h / 20 °C / Inert atmosphere; Irradiation

Reference： [1]Ji, Meishan; Chang, Chenyang; Wu, Xinxin; Zhu, Chen [Chemical Communications, 2021, vol. 57, # 73, p. 9240 - 9243]

70
[ 3507-26-4 ]
C₁₄H₁₀N₃OS⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: caesium carbonate / acetonitrile / 12 h / 60 °C / Inert atmosphere 2.1: hydrogenchloride / water / 1 h 2.2: 0.25 h / Inert atmosphere

Reference： [1]Ji, Meishan; Chang, Chenyang; Wu, Xinxin; Zhu, Chen [Chemical Communications, 2021, vol. 57, # 73, p. 9240 - 9243]

71
[ 3507-26-4 ]
[ 95-55-6 ]
C₁₄H₁₂N₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate In acetonitrile at 60℃; for 12h; Inert atmosphere;

Reference： [1]Ji, Meishan; Chang, Chenyang; Wu, Xinxin; Zhu, Chen [Chemical Communications, 2021, vol. 57, # 73, p. 9240 - 9243]

72
[ 3507-26-4 ]
(difluoromethyl)(2-isocyano-5-methylphenyl)sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: ethanol / 4 h / Reflux 2: sodium periodate; ruthenium trichloride / acetonitrile; tetrachloromethane; water / 5 h / 20 °C 3: cesium fluoride; water / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere; Schlenk technique