[ CAS No. 21303-50-4 ] {[proInfo.proName]}

Name: 21303-50-4|5-Methylbenzo[d]thiazole-2-thiol|97%
Brand: Ambeed
SKU: A156767
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Quality Control of [ 21303-50-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 21303-50-4 ]

CAS No. :	21303-50-4	MDL No. :	MFCD11044825
Formula :	C₈H₇NS₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ILDUPWKUQLPLKK-UHFFFAOYSA-N
M.W :	181.28	Pubchem ID :	10313387
Synonyms :

Safety of [ 21303-50-4 ]

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 [ 21303-50-4 ]

* 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 [ 21303-50-4 ]
Downstream synthetic route of [ 21303-50-4 ]

[ 21303-50-4 ] Synthesis Path-Upstream 1~7

1
[ 21303-50-4 ]
[ 14779-17-0 ]

Reference： [1] Gazzetta Chimica Italiana, 1946, vol. 76, p. 215,221

2
[ 13194-69-9 ]
[ 140-89-6 ]
[ 21303-50-4 ]

Yield	Reaction Conditions	Operation in experiment
73%	With iron(III) trifluoride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In N,N-dimethyl-formamide at 110℃; for 8 h; Inert atmosphere; Sealed tube	General procedure: A 25 mL reaction tube was charged with 2-haloaniline 1 (0.6 mmol), potassium o-ethyldithiocarbonate 2 (1.8 mmol), FeF3 (0.06 mmol), 2,2’-bis(diphenylphosphino)-1,1’-binaphthyl (0.03 mmol) and DMF (4 mL). The reaction vessel was flushed with argon for three times and sealed. Then the mixture was stirred electromagnetically in an oil bath at 110 for 3 - 21 hours. The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, then 4 mL HCl (3mol/L) was added and stirred for 30 minutes. Then the reaction mixture solution was extracted by ethyl acetate (3*20 mL). Subsequently, the combined organic solution were dried by anhydrous sodium sulfate and the target product was purified by silica gel colum chromatography (eluent: petroleum ether / ethylacetate) to give the corresponding pure product 3.

Reference： [1] Synthetic Communications, 2015, vol. 45, # 20, p. 2378 - 2385

3
[ 75-15-0 ]
[ 95-81-8 ]
[ 21303-50-4 ]

Yield	Reaction Conditions	Operation in experiment
27%	With potassium carbonate In N,N-dimethyl-formamide at 20 - 150℃; for 16 h;	5-Methyl-2-mercapto benzothiazole (10): To a suspension of 2-chloro-5 -methyl aniline (9, 1.00 g, 7.06 mmol) and K₂CO₃ (2.80 g, 28.2 mmol) in DMF (20 mL) was added CS₂ (0.50 mL, 8.50 mmol) under N₂ at room temperature. The reaction mixture was heated at 150 ⁰C for 16 h. After cooling, the reaction mixture was diluted with water (30 mL) and acidified with IN HCl. The precipitate was collected by filtration, washed with water, and dried over P₂O₅ under vacuum to yield compound 10 (0.35 g, 27percent).

Reference： [1] Patent: WO2006/122156, 2006, A2, . Location in patent: Page/Page column 126

4
[ 108-44-1 ]
[ 21303-50-4 ]

Reference： [1] Patent: US3967951, 1976, A,
[2] International Journal of Pharmacy and Pharmaceutical Sciences, 2017, vol. 9, # 2, p. 60 - 68

5
[ 53078-85-6 ]
[ 149-30-4 ]
[ 21303-50-4 ]

Reference： [1] Patent: US2003/139390, 2003, A1,

6
[ 75-15-0 ]
[ 638-03-9 ]
[ 21303-50-4 ]

Reference： [1] International Journal of Pharmacy and Pharmaceutical Sciences, 2017, vol. 9, # 2, p. 60 - 68

7
[ 89-60-1 ]
[ 21303-50-4 ]

Reference： [1] Patent: US5451594, 1995, A,

[ 21303-50-4 ] Synthesis Path-Downstream 1~30

1
[ 21303-50-4 ]
[ 14779-17-0 ]

Reference： [1]Gazzetta Chimica Italiana,1946,vol. 76,p. 215,221

2
[ 21303-50-4 ]
[ 3622-31-9 ]

Reference： [1]Patent: US1878699,1929,A
[2]Patent: DE516998,1928,C
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 17,p. 611
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 17,p. 611

3
[ 21303-50-4 ]
[ 2942-16-7 ]

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

4
[ 75-15-0 ]
[ 452-84-6 ]
[ 21303-50-4 ]

Reference： [1]European Journal of Medicinal Chemistry,1997,vol. 32,p. 397 - 408

6
[ 122-60-1 ]
[ 21303-50-4 ]
1-(5-methyl-1,3-benzothiazol-2-ylsulfanyl)-3-phenoxypropan-2-ol [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2005,vol. 41,p. 67 - 69

7
[ 21303-50-4 ]
[ 156740-78-2 ]
C₁₆H₁₄N₂O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In tetrahydrofuran; N,N-dimethyl-formamide; at 50℃; for 16h;	<strong>[21303-50-4]5-methyl-2-mercaptobenzothiazole</strong> (1.45 g, 8 mmol) was suspended in anhydrous THF (3.5 mL). A solution of potassium tert-butoxide (7.35 mL, 1.0 N in THF) was added in one portion. The very thick precipitate of the mercaptobenzothiazole potassium salt was dissolved by addition of DMF (1 mL). Triflate 80.1 (2 g, 6.7 mmol) was dissolved in DMF (1 mL) and added to the reaction mixture which was then heated to 50 C. for 16 h. The reaction mixture was pouted into 100 mL DI water and extracted 2×50 mL of ethyl acetate. The combined organic layers were washed with sat. brine, dried over MgSO4, filtered, concentrated, and the residue purified by flash chromatography (silica gel, 19:1 to 4:1 hexanes:ethyl acetate). Fractions containing the desired product were concentrated and the residue recrystallized from hot hexanes:ethyl acetetate. Filtration and drying provided the S-arylated compound 80.2 as bright yellow crystals (0.90 g). 1H NMR (CD3CN) delta 8.12 (s, 2H); 7.68 (d, 1H); 7.61 (s, 1H); 7.17 (d, 1H); 2.60 (s, 6H); 2.42 (s, 3H). MS (M+H) 331.1

Reference： [1]Patent: US2005/250820,2005,A1 .Location in patent: Page/Page column 44

9
polymer, polymerization degree = 50; monomer(s): (1S,2R,6S,7R)-4-benzyl-4-thionia-tricyclo[5.2.1.0^2,6]dec-8-ene perchlorate [ No CAS ]
[ 21303-50-4 ]
C₁₄H₁₁NS₂CH₂ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 3194 - 3198

10
[ 53078-85-6 ]
[ 149-30-4 ]
[ 21303-50-4 ]

Yield	Reaction Conditions	Operation in experiment
53%	In N,N-dimethyl-formamide;	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.

Reference： [1]Patent: US2003/139390,2003,A1

11
[ 176548-77-9 ]
[ 21303-50-4 ]
[ 315228-94-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With NaH; In N,N-dimethyl-formamide;	Example 264 1-[3-Chloro-2-(5-methyl-benzothiazol-2-ylsulfanyl)-5-nitro-phenyl]-ethanone (264) The title compound was prepared using the method of example 258, starting with 5-methyl-benzothiazole-2-thiol (245) (1.90 g, 10.5 mmol), 1-(2,3-dichloro-5-nitro-phenyl)-ethanone (248) (2.45 g, 10.5 mmol) and NaH (Aldrich, 60% suspension, 420 mg, 10.5 mmol) in DMF (20 mL). Compound 264 (3.87 g, 98%) was obtained as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 8.65 (d, J=2.3 Hz, 1H), 8.58 (d, J=2.5 Hz, 1H), 7.87 (d, J=8.3 Hz, 1H), 7.67 (br s, 1H), 7.24 (dd, J=8.2, 1.5 Hz, 1H), 2.65 (s, 3H), 2.41 (s, 3H). MS (M+H) 379.

Reference： [1]Patent: US2003/139390,2003,A1

12
[ 89-60-1 ]
[ 21303-50-4 ]

Yield	Reaction Conditions	Operation in experiment
		(viii) 2-mercapto-5-methylbenzthiazole yellow crystals mp 173-175 C. (from 4-chloro-3-nitrotoluene)

Reference： [1]Patent: US5451594,1995,A

13
[ 75-15-0 ]
[ 95-81-8 ]
[ 21303-50-4 ]

Yield	Reaction Conditions	Operation in experiment
27%	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 150℃; for 16h;	5-Methyl-2-mercapto benzothiazole (10): To a suspension of 2-chloro-5 -methyl aniline (9, 1.00 g, 7.06 mmol) and K2CO3 (2.80 g, 28.2 mmol) in DMF (20 mL) was added CS2 (0.50 mL, 8.50 mmol) under N2 at room temperature. The reaction mixture was heated at 150 0C for 16 h. After cooling, the reaction mixture was diluted with water (30 mL) and acidified with IN HCl. The precipitate was collected by filtration, washed with water, and dried over P2O5 under vacuum to yield compound 10 (0.35 g, 27%).

Reference： [1]Patent: WO2006/122156,2006,A2 .Location in patent: Page/Page column 126

14
[ 108-44-1 ]
[ 21303-50-4 ]

Yield	Reaction Conditions	Operation in experiment
55.5%	With carbon disulfide; hydrogen sulfide;	5-methyl-(2-mercapto)benzothiazole In an autoclave of 3 liters, 963g of m-toluidine, 820g of carbon disulfide and 288 g of sulfur were placed, the reaction was carried out at the temperature of 220 ~ 230C for 4 hours with stirring and the pressure in the autoclave was 50 kg/cm2. After cooling, 904g of 5-methyl-(2-mercapto)benzothiazole was obtained. (yield: 55.5%). Simultaneously, 487g of 7-methyl-(2-mercapto)benzothiazole as by-product was obtained.

Reference： [1]Patent: US3967951,1976,A
[2]International Journal of Pharmacy and Pharmaceutical Sciences,2017,vol. 9,p. 60 - 68

15
[ 21303-50-4 ]
5-methyl-2-(3'-t-butylamino-2'-hydroxypropylthio)benzothiazole hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; sodium hydroxide;	EXAMPLE 3 5-methyl-2-(3'-t-butylamino-2-hydroxypropylthio)benzothiazole hydrochloride. Eight grams of <strong>[21303-50-4]5-methyl-2-mercaptobenzothiazole</strong> was dissolved in 150 ml. of an equimolar aqueous sodium hydroxide solution and to this solution, 1-chloro3-t-butylaminopropanol-2 in 50 ml. of methanol was added dropwise under an atmosphere of nitrogen. Under the same atmosphere, the reaction solution stood at room temperature overnight and was extracted with chloroform after removal of excess methanol. The chloroform extract was dried in vacuo to give a pale reddish oil, which was purified by column chromatography on basic alumina and converted to its hydrochloride by a usual method. The hydrochloride was recrystallized from acetone-methanol to give needles of 5-methyl-2-(3'-t-butylamino-2-hydroxypropylthio)benzothiazole hydrochloride; mp 150 - 155C. C15 H22 N2 OS2.2HCl.H2 O:

Reference： [1]Patent: US3951998,1976,A

16
[ 21303-50-4 ]
[ 58790-62-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In methanol; sodium hydroxide; benzene-chloroform;	EXAMPLE 2 5-methyl-2-(3'-isopropylamino-2'-hydroxypropylthio)benzothiazole hydrochloride. Eight grams of <strong>[21303-50-4]5-methyl-2-mercaptobenzothiazole</strong> was dissolved in 130 ml. of an equimolar acqueous sodium hydroxide solution and to this solution, 5.5 g. of 1-chloro-3-isopropylaminopropanol-2 in 50 ml. of methanol was added dropwise. After addition of 100 ml. of methanol, the reaction solution stood at room temperature overnight and was condensed to a half volume to extract with chloroform. The chloroform extract was dried over anhydrous magnesium sulfate and evaporated to give an oil, which was dissolved in benzene-chloroform and treated with dry gaseous hydrogen chloride. Precipitated white crystals were collected and recrystallized from acetone-ethanol to give 5.6 g. of 5-methyl-2-(3'-isopropylamino-2'-hydroxypropylthio)benzothiazole hydrochloride; mp 147 - 149 C. C14 H20 ON2 S2.HCl:

Reference： [1]Patent: US3951998,1976,A

17
[ 13194-69-9 ]
[ 140-89-6 ]
[ 21303-50-4 ]

Yield	Reaction Conditions	Operation in experiment
73%	With iron(III) trifluoride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In N,N-dimethyl-formamide; at 110℃; for 8h;Inert atmosphere; Sealed tube;	General procedure: A 25 mL reaction tube was charged with 2-haloaniline 1 (0.6 mmol), potassium o-ethyldithiocarbonate 2 (1.8 mmol), FeF3 (0.06 mmol), 2,2?-bis(diphenylphosphino)-1,1?-binaphthyl (0.03 mmol) and DMF (4 mL). The reaction vessel was flushed with argon for three times and sealed. Then the mixture was stirred electromagnetically in an oil bath at 110 for 3 - 21 hours. The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, then 4 mL HCl (3mol/L) was added and stirred for 30 minutes. Then the reaction mixture solution was extracted by ethyl acetate (3*20 mL). Subsequently, the combined organic solution were dried by anhydrous sodium sulfate and the target product was purified by silica gel colum chromatography (eluent: petroleum ether / ethylacetate) to give the corresponding pure product 3.

Reference： [1]Synthetic Communications,2015,vol. 45,p. 2378 - 2385

18
anti-3-benzyl-3-methyl-6-oxabicyclo[3.1.0]hexane-2,4-dione [ No CAS ]
[ 21303-50-4 ]
(R)-2-benzyl-2-methyl-4-((5-methylbenzo[d]thiazol-2-yl)thio)cyclopent-4-ene-1,3-dione [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 5829 - 5833
Angew. Chem.,2016,vol. 128,p. 5923 - 5927,5

19
[ 21303-50-4 ]
C₁₀H₁₁N₃OS₂ [ No CAS ]