* 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.
With hydrazine hydrate In ethanol for 20 h; Reflux
To a solution of MBT (10.0 mmol) in ethanol (30 mL), hydrazine hydrate (5 mL, 80.0 mmol) was added. The reaction mixture was refluxed for 20 h, after cooling to room temperature the precipitate was filtered off, washed with cold ethanol, and ether followed by recrystallization from ethanol. Colorless crystals (1.23 g, 73.5percent yield), m.p. 198-200 °C, lit mp 199-200 °C [15].
60%
for 10 h; Reflux
Equimolar solution of 2-mercaptobenzothiazole (0.01 mol) and hydrazine hydrate (0.01 mol) in methanol (20 mL) was refluxed on a steam bath for about 10 h. The obtained filtrate was washed with ice water. The product was dried and recrystallized from ethanol to yield the pure compound (yield 60percent, m.p. 201-205 °C).
Reference：
[1] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 1, p. 67 - 74
[2] Journal of Chemical Crystallography, 2005, vol. 35, # 4, p. 293 - 296
[3] Indian Journal of Heterocyclic Chemistry, 2010, vol. 20, # 2, p. 163 - 166
[4] European Journal of Medicinal Chemistry, 2013, vol. 60, p. 503 - 511
[5] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995, vol. 34, # 7, p. 654 - 657
[6] Journal of the Indian Chemical Society, 1983, vol. 60, p. 475 - 478
[7] Medicinal Chemistry Research, 2013, vol. 22, # 11, p. 5105 - 5111
[8] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2015, vol. 151, p. 480 - 489
[9] Journal of the Indian Chemical Society, 2006, vol. 83, # 12, p. 1263 - 1266
[10] Revue Roumaine de Chimie, 2008, vol. 53, # 10, p. 911 - 919
[11] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2011, vol. 79, # 5, p. 1418 - 1424
[12] Indian Journal of Heterocyclic Chemistry, 2012, vol. 22, # 1, p. 47 - 52
[13] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 3, p. 418 - 429
[14] Journal of the Chemical Society of Pakistan, 2016, vol. 38, # 2, p. 301 - 306
[15] Inorganica Chimica Acta, 2017, vol. 466, p. 625 - 631
[16] Journal of Molecular Structure, 2017, vol. 1149, p. 357 - 366
[17] Archiv der Pharmazie, 2018, vol. 351, # 3-4,
[18] Acta Poloniae Pharmaceutica - Drug Research, 2018, vol. 75, # 3, p. 625 - 636
[19] Asian Journal of Chemistry, 2018, vol. 30, # 12, p. 2608 - 2614
[20] Journal of Molecular Structure, 2019, vol. 1179, p. 65 - 75
2
[ 149-30-4 ]
[ 615-21-4 ]
Reference：
[1] Journal of the Chemical Society, 1949, p. 355,361
3
[ 149-30-4 ]
[ 2942-06-5 ]
Reference：
[1] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 1394 - 1397[2] Zhurnal Obshchei Khimii, 1960, vol. 30, p. 1363 - 1366
[3] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 1394 - 1397[4] Zhurnal Obshchei Khimii, 1960, vol. 30, p. 1363 - 1366
4
[ 149-30-4 ]
[ 615-20-3 ]
Yield
Reaction Conditions
Operation in experiment
90%
Stage #1: at 20 - 25℃; for 0.25 h; Inert atmosphere Stage #2: at 20 - 25℃; for 3 h; Inert atmosphere
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.2-Chlorobenzo[d]thiazole (13)Yield: 3.30 g, 19.5 mmol (90percent); yellow oil.1 H NMR (400 MHz, DMSO-d 6 ): δ = 7.45–7.62 (m, 2 H), 7.96 (dd, J =8.07, 0.73 Hz, 1 H), 8.09 (dd, J = 7.89, 0.92 Hz, 1 H).13 C NMR (101 MHz, DMSO-d 6 ): δ = 122.81, 122.86, 126.49, 127.47,136.19, 150.91, 153.23. HRMS (ESI): m/z [M + H] + calcd for C 7 H 5 ClNS: 169.9831; found:169.9844.
36.1 g
With hydrogenchloride; dihydrogen peroxide In water at 38℃; for 4 h;
In a 500 ml reaction flask, 36.4 g of 2-mercaptobenzothiazole and 80 g of water were cast, 29.7 g of 30percent hydrochloric acid was added, the temperature was raised to 38 ° C,48.5g mass fraction of 20percent hydrogen peroxide was added dropwise, after the end of incubation was incubated dropwise to detect the bodyWhen the content of 2-mercaptobenzothiazole in the system is less than 0.2percent, hydrogen peroxide (about 4h)After the reaction was settled stratification,The upper oily liquid is 2 - chlorobenzothiazole crude,Finally, anhydrous 2 - chlorobenzothiazole dry crude product obtained2-Chlorobenzothiazole fine 36.1g.
Reference：
[1] Synthesis (Germany), 2018, vol. 50, # 10, p. 2027 - 2032
[2] Bulletin of the Chemical Society of Japan, 1992, vol. 65, # 11, p. 3163 - 3173
[3] , 1965, vol. 1, p. 1702 - 1704[4] Zhurnal Organicheskoi Khimii, 1965, vol. 1, p. 1679 - 1682
[5] Synthetic Communications, 2007, vol. 37, # 12, p. 2039 - 2050
[6] Patent: CN107129484, 2017, A, . Location in patent: Paragraph 0019; 0014; 0015; 0016; 0017; 0018
5
[ 149-30-4 ]
[ 615-20-3 ]
Reference：
[1] Pharmaceutical Bulletin, 1953, vol. 1, p. 319,321
[2] Zhurnal Obshchei Khimii, 1937, vol. 7, p. 2813,2815[3] Chem. Zentralbl., 1938, vol. 109, # II, p. 3084
[4] Patent: US1757930, 1927, ,
[5] Patent: US1923957, 1929, ,
[6] Patent: US2043948, 1933, ,
[7] Journal of Organic Chemistry, 1937, vol. 2, p. 148,153
[8] Journal of the American Chemical Society, 1946, vol. 68, p. 1666
[9] Patent: US2469697, 1946, ,
[10] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 611
[11] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 611
6
[ 149-30-4 ]
[ 615-20-3 ]
[ 4074-77-5 ]
Reference：
[1] Zhurnal Obshchei Khimii, 1937, vol. 7, p. 2813,2815[2] Chem. Zentralbl., 1938, vol. 109, # II, p. 3084
7
[ 149-30-4 ]
[ 1123-55-3 ]
Reference：
[1] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 1394 - 1397[2] Zhurnal Obshchei Khimii, 1960, vol. 30, p. 1363 - 1366
8
[ 149-30-4 ]
[ 6285-57-0 ]
Reference：
[1] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 1394 - 1397[2] Zhurnal Obshchei Khimii, 1960, vol. 30, p. 1363 - 1366
[3] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 1394 - 1397[4] Zhurnal Obshchei Khimii, 1960, vol. 30, p. 1363 - 1366
9
[ 149-30-4 ]
[ 2407-11-6 ]
Reference：
[1] Yakugaku Zasshi, 1946, vol. 66, p. Ausg. B, S. 75[2] Chem.Abstr., 1952, p. 112
[3] Zhurnal Obshchei Khimii, 1937, vol. 7, p. 2813,2815[4] Chem. Zentralbl., 1938, vol. 109, # II, p. 3084
[5] Yakugaku Zasshi, 1946, vol. 66, p. Ausg. B, S. 75[6] Chem.Abstr., 1952, p. 112
10
[ 149-30-4 ]
[ 6973-51-9 ]
Reference：
[1] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 1394 - 1397[2] Zhurnal Obshchei Khimii, 1960, vol. 30, p. 1363 - 1366
11
[ 149-30-4 ]
[ 101-83-7 ]
[ 4979-32-2 ]
Yield
Reaction Conditions
Operation in experiment
96.2%
Stage #1: at 50℃; for 2 h; Stage #2: With hydrogenchloride In water at 35℃; Stage #3: With sodium hypochlorite In water; toluene at 30℃; for 0.000555556 h;
(1) Disposing an M-Na salt solution: mixing 400 g of the promoter MBT with 360 g of a 32 wtpercent NaOH solution, and stirring at 50 ° C for 2 h to prepare an M-Na salt solution;A hydrochloric acid solution of cyclohexylamine was placed: 567 g of dicyclohexylamine was mixed with 376 g of industrial hydrochloric acid having a concentration of 31percent by weight.Adding 567 g of water and stirring at 35 ° C to obtain a hydrochloric acid solution of cyclohexylamine;(2) M-Na salt solution, dicyclohexylamine hydrochloric acid solution,Solvent toluene and sodium hypochlorite solution with 17percent effective chlorine content according to M-Na salt solution 69mL/min,Dihydrohexylamine hydrochloride solution 136mL / min,Toluene 130mL / min and sodium hypochlorite solution 49mL / min speed into the microchannel reactor for oxidation reaction, the reaction residence time is 2s, the reaction temperature is 30 ° C, the microchannel reactor is 4 reactors in series,The volume of each reactor was 3.2 mL, and the total volume of the reactor after the series was 12.8 mL;(4) Collecting the material flowing out of the reactor, and crystallization after stirring to a temperature of 5 ° C;The crude product is washed once with 200 mL of isopropyl alcohol aqueous solution and washed twice with 200 mL of water to obtain DCBS wet material. After drying, DCBS finished product can be obtained.The DCBS yield of this example was determined to be 96.2percent (based on the content of MBT), the purity of DCBS was 99.2percent by weight, and the appearance was a pale yellow powder. After the waste water was continuously distilled to recover isopropanol, the residual COD was 5900 ppm.
Reference：
[1] Patent: CN108586383, 2018, A, . Location in patent: Paragraph 0069-0075; 0080; 0087; 0094; 0101
[2] Phosphorus and Sulfur and the Related Elements, 1988, vol. 35, p. 311 - 318
12
[ 108-91-8 ]
[ 149-30-4 ]
[ 4979-32-2 ]
Yield
Reaction Conditions
Operation in experiment
61.2%
at 45℃;
General procedure: To a stirred solution of benzothiazole-2-thiol (1equiv) and cyclohexylamine (2.5equiv), the sodium hypochlorite solution was added slowly at 45°C. The completion of oxidation was confirmed by bluestone solution and KI starch solution. The reaction solution was cooled to room temperature and the precipitate was separated out. Then precipitate was washed by 9percent cyclohexylamine aqueous solution. Without further purification, the precipitate was filtered off to give the products.
Reference：
[1] European Journal of Medicinal Chemistry, 2015, vol. 93, p. 423 - 430
13
[ 149-30-4 ]
[ 101-83-7 ]
[ 7757-83-7 ]
[ 4979-32-2 ]
Reference：
[1] Patent: EP314663, 1989, A1,
14
[ 53078-85-6 ]
[ 149-30-4 ]
[ 21303-50-4 ]
Reference：
[1] Patent: US2003/139390, 2003, A1,
15
[ 149-30-4 ]
[ 120-78-5 ]
[ 4845-58-3 ]
Reference：
[1] Patent: US4975448, 1990, A,
16
[ 149-30-4 ]
[ 4845-58-3 ]
Reference：
[1] Agricultural and Biological Chemistry, 1987, vol. 51, # 7, p. 1941 - 1946
[2] ChemMedChem, 2011, vol. 6, # 4, p. 654 - 666
17
[ 80756-85-0 ]
[ 65872-41-5 ]
[ 149-30-4 ]
Reference：
[1] Journal of Organic Chemistry, 1994, vol. 59, # 24, p. 7259 - 7266
18
[ 14814-09-6 ]
[ 120-78-5 ]
[ 149-30-4 ]
[ 56706-10-6 ]
Reference：
[1] Patent: US5675014, 1997, A,
19
[ 120-78-5 ]
[ 86299-47-0 ]
[ 89604-92-2 ]
[ 149-30-4 ]
Reference：
[1] Research on Chemical Intermediates, 2013, vol. 39, # 2, p. 615 - 620
Example 245 2-Mercapto -5-Methyl-benzothiazole (245) The title compound was prepared using the method of Example 239, starting with 2-bromo-5-methyl-phenylamine (244) (4.48 g, 24.0 mmol), O-ethylxanthic acid, potassium salt (Lancaster, 8.70 g, 54 mmol) in DMF (35 mL). The mercaptobenzothiazole 245 was obtained as an pale brown solid (2.31 g, 53%). 1H NMR (DMSO-d6) delta 13.70 (br s, 1H), 7.56 (d, J=8.6 Hz, 1H), 7.15-7.10 (m, 2H), 2.38 (s, 3H). MS (M-H) 180.
In tetrahydrofuran; tetrachloromethane; petroleum;
This product (185 g) was dissolved in carbon tetrachloride (1250 ml). N-Bromosuccinimide (159.3) was added and the mixture heated under reflux for 3 hours. The reaction mixture was then cooled and worked up to give a light brown oil. The crude product was triturated with a 10% solution of di-isopropyl ether in light petroleum to give methyl (E)-3-methoxy-2-[(2-bromomethyl)phenyl]prop-2-enoate, m.p. 87-90 C. 2-Mercaptobenzothiazole (101.87 g) in tetrahydrofuran (600 ml) was added dropwise with stirring to a petrol washed suspension of sodium hydride (from 18.42 g of 80% dispersion in oil), in tetrahydrofuran (200 ml). The mixture was heated under reflux for 30 minutes and cooled to room temperature. A solution of the bromomethyl compound (175 g) in tetrahydrofuran (1000 ml) was added over one hour and the mixture stirred for 5 hours at room temperature. Aqueous tetrahydrofuran was added to quench the reaction and the mixture was evaporated. The residue was worked up in conventional manner to give methyl (E)-2-[2-[[(2-benzothiazolyl)thio]-methyl]phenyl]-3-methoxy-2-propenoate, m.p. 77-78. (Compound 1).
EXAMPLE 46 2.3 g of sodium is dissolved in 250 ml of ethanol; 13.5 g of 2-mercaptobenzothiazole, followed by 17.1 g of 2-chloro-2-phenylacetic acid, is added and the mixture is boiled under reflux for 6 hours. It is then cooled, the sodium salt which has precipitated is filtered off and dissolved in water; and the solution is washed with water, acidified with hydrochloric acid and worked up in the customary manner. This gives 2-(benzothiazol-2-ylthio)-2-phenylacetic acid, m.p. 152-154.
Example 1: A 50 ml sample of triethylamine is added to a 0.5 1, three necked glass reactor, equipped with condenser and mechanical stirrer with 100 ml of acetone, and cooled to about 10 to about 15C. Under mixing, 50 g of azetidine is added to the reaction mixture, followed by 43g of TAEM. Stirring is continued for at least about 30 minutes, until the initially formed color disappears. Two additional 43 g portions of TAEM are then added in the same manner. After the reaction ends, typically after about four hours, water is added to quench the reaction, and the acetone is removed by distillation with the water. The reaction mass is acidified with HCl to a pH of about 5.5, and cooled. Mercaptobenzothiazole (MBT) precipitates, and is separated by filtration. The pH of the reaction mass containing tertbutylaztreonam is adjusted to about1.5 with HCl, and diluted with about 400 ml of water. The reaction mass is heated to about 600C and maintained at that temperature for about 5 hours. After verifying chromatographically that the deprotection reaction has ended, the reaction mass is cooled slowly over a period of about 5 hours to about 0 to about 5C. Aztreonam precipitates, and is filtered and washed several times with water. The filter cake is recharged, slurried with 240 ml of absolute ethanol, filtered again, and discharged. About 14Og of wet aztreonam crude is obtained.
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 0 - 20℃; for 18h;
a) (S)-4-(Benzothiazol-2-ylsulfanyl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester <n="69"/>To a stirred, cooled (00C) solution of (R)-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3- carboxylic acid tert-butyl ester (1.36 g; CAS 108149-65-1), 2-mercaptobenzothiazole (1.48 g) and triphenylphosphine (2.32 g) in THF (80 ml) under an argon atmosphere was added diethyl azodicarboxylate (4.1 ml; 40% solution in toluene). The mixture (soon turning to a yellow suspension, slowly warming up to r.t.) was stirred for 18 h overnight, then diluted with EtOAc and washed with sat. aq. Na2CO3. The aqueous phase was back extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (Sitheta2; gradient: cyclohexane -> cyclohexane/EtOAc 85:15) to give (S) -4- (benzothiazol-2-ylsulfanyl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (2.0 g) as light yellow viscous oil.
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 0 - 20℃;Inert atmosphere;
To a stirred, cooled (0 C.) solution of (S)-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.36 g), 2-mercaptobenzothiazole (1.48 g) and triphenylphosphine (2.32 g) in THF (80 ml) under an argon atmosphere was added diethyl azodicarboxylate (4.1 ml; 40% solution in toluene). The mixture (soon turning to a yellow suspension, slowly warming up to r.t.) was stirred for 18 h overnight, then diluted with EtOAc and washed with sat. aq. Na2CO3. The aqueous phase was back extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (SiO2; gradient: cyclohexane->cyclohexane/EtOAc 85:15) to give (R)-4-(benzothiazol-2-ylsulfanyl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (2.1 g) as light yellow viscous oil.
With sodium hydride; In 1-methyl-pyrrolidin-2-one; at 10 - 150℃; for 13h;
Example 4Production of 4,4'-Di(2-benzothiazolylthio)diphenyl Sulfone4,4'-Dichlorodiphenyl sulfone (14.4 g, 50 mmol), 2-benzothiazolethiol (17.6 g, 105 mmol), and N-methylpyrrolidone (100.0 g) were placed in a 500 mL-flask equipped with a stirrer, a thermometer, a condenser, and a gas inlet tube; sodium hydride (4.2 g, 105 mmol) was dividedly added thereto while maintaining the temperature of the solution at 10 C.; and the temperature of the solution was raised to 150 C. under stirring to perform reaction for 13 hours.After the reaction was completed, the temperature of the solution was cooled to 10 C., and water (257 g) was added dropwise thereto. Subsequently, the reaction solution was filtered, thereby obtaining 4,4'-di(2-benzothiazolylthio)diphenyl sulfone (16.7 g). The yield relative to 4,4'-dichlorodiphenyl sulfone was 90%.1H NMR d 7.35-7.49 (m, 4H), 7.73-7.79 (m, 6H), 7.92-8.00 (m, 6H);Elemental analysis (as C26H16N2O2S5);Calculated: C, 56.91%; H, 2.94%; N, 5.11%; O: 5.83%; S: 29.22%.Found C, 56.87%; H, 2.91%; N, 5.14%; O: 5.88%; S: 29.21%.Refractive index: 1.692
2-{2-[(benzo[d]thiazol-2-ylthio)ethyl]phenyl}acetaldehyde[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
75%
With di-tert-butyl peroxide; In neat (no solvent); at 120℃; for 6h;
General procedure: A sealed tube was charged with isochroman (or benzylic ether;1 mmol), DTBP (1.5 mmol), thiol (or thiophenol; 1.5 mmol). Thereaction mixture was stirred at 120 C for 6 h. The reactionmixture was then cooled to obtain a brown liquid. The organicsolutions could be purified directly by column chromatographyon silica gel to give the pure product (hexane-EtOAc, 20:1).
2.1 g (0.01 mol) of <strong>[2516-40-7]2-<strong>[2516-40-7]bromobenzothiazole</strong></strong> and 1.2 g of sodium hydrosulfide were added to 50 mL of anhydrous ethanol and heated to refluxThe filtrate was concentrated, washed several times, filtered and dried to give 1.6 g of an off-white solid, yield: 76.1percent
7%
With thiourea; In ethanol; for 13h;Reflux;
General procedure: The corresponding halide reagent (1mmol) was added to a mixture of thiourea (1.1mmol) (compounds a) or selenourea (compounds b) in absolute ethanol or dry methanol (20mL) for compound 1b. The mixture was stirred at reflux for 0.5?15h. The product was isolated by filtration or by rotatory evaporation of the solvent under vacuum and purified by recrystallization, washing or column chromatography.
1-(benzo[d]thiazol-2-ylthio)-3-(3-chlorophenyl)propan-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
89%
With dipotassium peroxodisulfate; potassium iodide; In dimethyl sulfoxide; at 20℃; for 24h;Schlenk technique;
1.0 mmol of <strong>[14123-60-5]3-chlorophenylacetone</strong>,0.5 mmol of mercaptobenzothiazole,20 mol% of potassium iodide, 0.3 mmol of potassium persulfate, 1 ml of DMSO was added to the Schlenk tube under an air atmosphere and stirred at room temperature for 24 hours. After completion of the reaction, the separation and purification gave 2- (benzo [d] thiazol-2-ylthio) -1- (3-chlorophenyl) acetone in 89% isolated yield. The product was identified by 1H, 13C NMR.
2-((pyrimidin-2-ylmethyl)thio)benzo[d]thiazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
77%
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20℃;
To a solution of <strong>[42839-09-8]pyrimidin-2-ylmethanol</strong> (16.6 g, 151 mmol, 1 equiv), benzo[d]thiazole- 2-thiol (30 g, 181 mmol, 1.2 equiv) and PPh3 (47.4 g, 181 mmol, 1.2 equiv) in THF (500 mL) was added DEAD (36.6 g, 181 mmol, 1.2 equiv) at 0C. The mixture was stirred at room temperature for 16 hours. The reaction mixture was treated with HC1 solution in dioxane and the white precipitate was collected via filtration. The solid was charged with 1N NaiCOi aqueous solution (100 mL) and extracted with EtOAc (3*200 mL). The combined organic phase were concentrated in vacuo to afford the title compound 2- ((pyrimidin-2-ylmethyl)thio)benzo[d]thiazole as a yellow solid (27 g, 77% yield). LC-MS: m/z 260.0 (M+H)+
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