[ CAS No. 3622-38-6 ] {[proInfo.proName]}

Name: 3622-38-6|2-Chloro-5-nitrobenzo[d]thiazole|97%
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Quality Control of [ 3622-38-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3622-38-6 ]

SDS Specification

Alternatived Products of [ 3622-38-6 ]

Product Details of [ 3622-38-6 ]

CAS No. :	3622-38-6	MDL No. :	MFCD09540490
Formula :	C₇H₃ClN₂O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BSHJRTMGKFPQGZ-UHFFFAOYSA-N
M.W :	214.63	Pubchem ID :	11413249
Synonyms :

Calculated chemistry of [ 3622-38-6 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	53.45
TPSA :	86.95 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.18 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.5
Log Po/w (XLOGP3) :	3.42
Log Po/w (WLOGP) :	2.86
Log Po/w (MLOGP) :	1.73
Log Po/w (SILICOS-IT) :	1.59
Consensus Log Po/w :	2.22

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.77
Solubility :	0.0363 mg/ml ; 0.000169 mol/l
Class :	Soluble
Log S (Ali) :	-4.93
Solubility :	0.00254 mg/ml ; 0.0000119 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-2.97
Solubility :	0.228 mg/ml ; 0.00106 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.45

Safety of [ 3622-38-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3622-38-6 ]

* 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 [ 3622-38-6 ]
Downstream synthetic route of [ 3622-38-6 ]

[ 3622-38-6 ] Synthesis Path-Upstream 1~8

1
[ 615-20-3 ]
[ 3622-38-6 ]
[ 2407-11-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	With sulfuric acid; nitric acid In water at 0 - 5℃; for 3.33333 h;	To a solution of 2-CHLOROBENZOTHIAZOLE (12.0 g, 70.7 MMOL) in concentrated H2SO4 (60 mL) was added HN03 (69percent solution, 6 mL) dropwise at 0°C for 20 min. The mixture was stirred at 5°C for 3h, poured into ice-water (150 mL). The precipitate was collected and washed with 5percent sodium bicarbonate and water, dried in VACUO.APOS;H NMR analysis showed the mixture contained 78percent 6-nitro-2-chlorobenzothiazole and 8percent 5-nitro-2- chlorobenzothiazole. Recrystallization from ethanol gave 6-nitro-2-chlorobenzothiazole as white crystalline solid (11 g, 72percent). 3.5 g of the solid was dissolved in refluxing ethanol-acetic acid (150: 15 mL), Iron powder was added in one portion.. The mixture was refluxed for 1.5h, filtered. The filtrate was concentrated in vacuo to half volume and neutralized with 10percent NaOH to pH 7.5, extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulphate and evaporated to give a residue, which was RECRYSTALLIZED from ethanol. Light purple crystals (2.5 g, 83percent) were obtained. Mp 160-164°C ; TLC single spot at Rf 0.27 (30percent EtOAc/hexane) ;APOS;HNMR (270 MHz, DMSO-d6) 5 7.58 (1H, d, J = 9.0 Hz, 4-H), 7.03 (1H, d, J = 2.0 Hz, 7-H), 6.77 (1 H, dd, J = 9.0, 2. 0 Hz, 5-H), 5.55 (2H, s, NH2). The mother liquor from the RECRYSTALLIZATION of nitration product was evaporated and subjected to iron powder reduction as described above. The crude product was purified with flash chromatography (ethyl acetate-DCM gradient elution) to give 2-CHLORO- benzothiazol-5-yl-amine as yellow solid. Mp 146-149°C ; TLC single spot at Rf 0.52 (10percent EtOAc/DCM) ;APOS;HNMR (270 MHZ, DMSO-d6) 8 7.63 (1 H, d, J = 8. 6 HZ, 7-H), 7.05 (1 H, d, J = 2.3 Hz, 4-H), 6.78 (1 H, dd, J = 8.6, 2.3 Hz, 6-H), 5.40 (2H, s, NH2).

Reference： [1] Patent: WO2004/37251, 2004, A1, . Location in patent: Page/Page column 99; 100

2
[ 3622-38-6 ]
[ 80945-82-0 ]

Yield	Reaction Conditions	Operation in experiment
1.55 g	With iron; acetic acid In ethanol for 1.5 h; Reflux	o a solution of 2-chloro-5-nitrobenzo[d]thiazole (2.18 g, 10.2 mmol) in EtOH:acetic acid 91 :9 (102 mL) iron powder (5.70 g, 102 mmol) was carefully added. The mixture was refluxed for 1 .5 h before it was filtered. The filtrate was concentrated to about one third of the volume and the pH of the solution was adjusted to pH 8 by adding 10percent aq. NaOH solution. The mixture was extracted with EA (150 mL). The organic extract was washed with brine, dried over Na₂S0₄, filtered and concentrated. The crude product was suspended in EtOH (4 mL), filtered, washed with additional EtOH (0.5 mL) and dried to give the title compound (1 .55 g) as a solid; LC-MS: t_R= 0.78 min; [M+H]⁺= 185.03;¹H NMR (400 MHz, D₆-DMSO) δ: 7.65 (d, J = 8.7 Hz, 1 H), 7.06 (d, J = 1 .9 Hz, 1 H), 6.79 (dd, J, = 2.0 Hz, J₂= 8.7 Hz, 1 H), 5.43 (s, 2 H).

Reference： [1] Journal of medicinal chemistry, 1972, vol. 15, # 5, p. 523 - 529
[2] Patent: WO2016/207785, 2016, A1, . Location in patent: Page/Page column 46

3
[ 58759-63-0 ]
[ 3622-38-6 ]

Yield	Reaction Conditions	Operation in experiment
38%	With sulfuryl dichloride In dichloromethane at 20℃; for 1 h; Cooling with ice	General procedure: GP3-1: A solution of 2-halo substituted aniline (1.0 eq), potassium ethyl xanthate (1.2 eq or 2.2 eq,typically 2.2 eq) in 10 volume of anhydrous DMF was heated at 100 ⁰Cor 120 ⁰C for 4 hours under nitrogen. TLC monitored the progress ofreaction. After completion, the reaction mixture was cooled to room temperature,diluted with water (10 volume) and neutralized by 1 M HCl solution to pH 5. Theformed precipitate was collected by filtration, rinsed with water, firstlydried by rotavapor, and then dried by oil pump to afford 2-mercaptobenzothiazole.GP3-2: 2-mercaptobenzothiazole in 10 volume ofanhydrous DCM, was added by sulfuryl chloride (SO₂Cl₂, 1volume) under ice-cooled condition. The mixture was stirred at rt for 1 hour,which was monitored by TLC. After consumption of starting material, the mixturewas diluted by 30 volume of ether, following quenching carefully by addingwater. Stirring was kept for 1 hour to make sure the SO₂Cl₂was totally consumed and product was released. Organic layer was collected,neutralized by saturated NaHCO₃, dried over Na₂SO₄and purified by silica gel chromatograph to give the pure product, which wasfinally characterized by LC-MS and NMR.
2.02 g	at 0 - 20℃; for 2 h;	Solid 5-nitrobenzo[d]thiazole-2-thiol (4.0 g, 18.8 mmol) was placed in a round bottom flask and cooled to 0°C while S0₂CI₂(9.1 mL, 1 13 mmol) was slowly added at 0°C. Upon complete additions, the yellow suspension was stirred at 0°C for 5 min, then at rt for 2 h. The mixture was poured onto ice/water (200 mL) and stirred for 1 h. The precipitate that formed was collected, washed with water and dried under high vacuum. The material was slurried in EA (25 mL), vigorously stirred for 15 min and filtered. The filtrate was concentrated and dried. The obtained solid absorbed to silica gel and purified by CC eluting with heptane:EA 4:1 to give the title compound (2.02 g) as a solid; LC-MS: t_R= 0.84 min; [M+H]⁺= 214.51 ;¹H NMR (400 MHz, CDCI₃) δ: 8.84 (d, J = 2.2 Hz, 1 H), 8.35 (dd, J, = 2.2 Hz, J₂= 8.9 Hz, 1 H), 7.98 (d, J = 8.9 Hz, 1 H).

Reference： [1] Journal of Heterocyclic Chemistry, 2005, vol. 42, # 4, p. 727 - 730
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7661 - 7670
[3] Patent: WO2016/207785, 2016, A1, . Location in patent: Page/Page column 45; 46

4
[ 615-20-3 ]
[ 3622-38-6 ]
[ 2407-11-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	With sulfuric acid; nitric acid In water at 0 - 5℃; for 3.33333 h;	To a solution of 2-CHLOROBENZOTHIAZOLE (12.0 g, 70.7 MMOL) in concentrated H2SO4 (60 mL) was added HN03 (69percent solution, 6 mL) dropwise at 0°C for 20 min. The mixture was stirred at 5°C for 3h, poured into ice-water (150 mL). The precipitate was collected and washed with 5percent sodium bicarbonate and water, dried in VACUO.APOS;H NMR analysis showed the mixture contained 78percent 6-nitro-2-chlorobenzothiazole and 8percent 5-nitro-2- chlorobenzothiazole. Recrystallization from ethanol gave 6-nitro-2-chlorobenzothiazole as white crystalline solid (11 g, 72percent). 3.5 g of the solid was dissolved in refluxing ethanol-acetic acid (150: 15 mL), Iron powder was added in one portion.. The mixture was refluxed for 1.5h, filtered. The filtrate was concentrated in vacuo to half volume and neutralized with 10percent NaOH to pH 7.5, extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulphate and evaporated to give a residue, which was RECRYSTALLIZED from ethanol. Light purple crystals (2.5 g, 83percent) were obtained. Mp 160-164°C ; TLC single spot at Rf 0.27 (30percent EtOAc/hexane) ;APOS;HNMR (270 MHz, DMSO-d6) 5 7.58 (1H, d, J = 9.0 Hz, 4-H), 7.03 (1H, d, J = 2.0 Hz, 7-H), 6.77 (1 H, dd, J = 9.0, 2. 0 Hz, 5-H), 5.55 (2H, s, NH2). The mother liquor from the RECRYSTALLIZATION of nitration product was evaporated and subjected to iron powder reduction as described above. The crude product was purified with flash chromatography (ethyl acetate-DCM gradient elution) to give 2-CHLORO- benzothiazol-5-yl-amine as yellow solid. Mp 146-149°C ; TLC single spot at Rf 0.52 (10percent EtOAc/DCM) ;APOS;HNMR (270 MHZ, DMSO-d6) 8 7.63 (1 H, d, J = 8. 6 HZ, 7-H), 7.05 (1 H, d, J = 2.3 Hz, 4-H), 6.78 (1 H, dd, J = 8.6, 2.3 Hz, 6-H), 5.40 (2H, s, NH2).

Reference： [1] Patent: WO2004/37251, 2004, A1, . Location in patent: Page/Page column 99; 100

5
[ 369-36-8 ]
[ 3622-38-6 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2005, vol. 42, # 4, p. 727 - 730
[2] Patent: WO2016/207785, 2016, A1,

6
[ 73458-39-6 ]
[ 3622-38-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 9, p. 2540 - 2544

7
[ 6283-25-6 ]
[ 3622-38-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7661 - 7670

8
[ 80945-80-8 ]
[ 3622-38-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 9, p. 2540 - 2544

[ 3622-38-6 ] Synthesis Path-Downstream 1~39

1
[ 3622-38-6 ]
[ 80945-82-0 ]

Yield	Reaction Conditions	Operation in experiment
1.55 g	With iron; acetic acid; In ethanol; for 1.5h;Reflux;	o a solution of <strong>[3622-38-6]2-chloro-5-nitrobenzo[d]thiazole</strong> (2.18 g, 10.2 mmol) in EtOH:acetic acid 91 :9 (102 mL) iron powder (5.70 g, 102 mmol) was carefully added. The mixture was refluxed for 1 .5 h before it was filtered. The filtrate was concentrated to about one third of the volume and the pH of the solution was adjusted to pH 8 by adding 10percent aq. NaOH solution. The mixture was extracted with EA (150 mL). The organic extract was washed with brine, dried over Na2S04, filtered and concentrated. The crude product was suspended in EtOH (4 mL), filtered, washed with additional EtOH (0.5 mL) and dried to give the title compound (1 .55 g) as a solid; LC-MS: tR= 0.78 min; [M+H]+= 185.03;1H NMR (400 MHz, D6-DMSO) delta: 7.65 (d, J = 8.7 Hz, 1 H), 7.06 (d, J = 1 .9 Hz, 1 H), 6.79 (dd, J, = 2.0 Hz, J2= 8.7 Hz, 1 H), 5.43 (s, 2 H).

Reference： [1]Journal of medicinal chemistry,1972,vol. 15,p. 523 - 529
[2]Patent: WO2016/207785,2016,A1 .Location in patent: Page/Page column 46

Yield	Reaction Conditions	Operation in experiment
38%	With sulfuryl dichloride; In dichloromethane; at 22℃; for 1.0h;Cooling with ice;	General procedure: GP3-2: 2-mercaptobenzothiazole in 10 volume of anhydrous DCM, was added by sulfuryl chloride (SO2Cl2, 1 volume) under ice-cooled condition. The mixture was stirred at rt for 1 hour, which was monitored by TLC. After consumption of starting material, the mixture was diluted by 30 volume of ether, following quenching carefully by adding water. Stirring was kept for 1 hour to make sure the SO2Cl2 was totally consumed and product was released. Organic layer was collected, neutralized by saturated NaHCO3, dried over Na2SO4 and purified by silica gel chromatograph to give the pure product, which was finally characterized by LC-MS and NMR.; 2-chloro-7-fluorobenzothiazole The title compound was prepared according to GP3-2, which was purified by flash column chromatography using PE/EA (20/1) as eluent to give the colorless oil. (420 mg, 22percent yield) 1H NMR (400 MHz, CDCl3) delta 7.76 (d, J=8.2 Hz, 1H), 7.45 (td, J=8.1, 5.9 Hz, 1H), 7.14 (t, J=8.7 Hz, 1H). 13C NMR (101 MHz, CDCl3) delta 156.11 (d, J=250.1 Hz), 154.27, 153.45 (d, J=2.8 Hz), 127.63 (d, J=7.3 Hz), 123.25 (d, J=17.6 Hz), 118.80 (d, J=3.7 Hz), 111.41 (d, J=18.3 Hz).

4
[ 58759-63-0 ]
[ 3622-38-6 ]

Yield	Reaction Conditions	Operation in experiment
38%	With sulfuryl dichloride; In dichloromethane; at 20℃; for 1.0h;Cooling with ice;	General procedure: GP3-1: A solution of 2-halo substituted aniline (1.0 eq), potassium ethyl xanthate (1.2 eq or 2.2 eq,typically 2.2 eq) in 10 volume of anhydrous DMF was heated at 100 0Cor 120 0C for 4 hours under nitrogen. TLC monitored the progress ofreaction. After completion, the reaction mixture was cooled to room temperature,diluted with water (10 volume) and neutralized by 1 M HCl solution to pH 5. Theformed precipitate was collected by filtration, rinsed with water, firstlydried by rotavapor, and then dried by oil pump to afford 2-mercaptobenzothiazole.GP3-2: 2-mercaptobenzothiazole in 10 volume ofanhydrous DCM, was added by sulfuryl chloride (SO2Cl2, 1volume) under ice-cooled condition. The mixture was stirred at rt for 1 hour,which was monitored by TLC. After consumption of starting material, the mixturewas diluted by 30 volume of ether, following quenching carefully by addingwater. Stirring was kept for 1 hour to make sure the SO2Cl2was totally consumed and product was released. Organic layer was collected,neutralized by saturated NaHCO3, dried over Na2SO4and purified by silica gel chromatograph to give the pure product, which wasfinally characterized by LC-MS and NMR.
2.02 g	With thionyl chloride; at 0 - 20℃; for 2.0h;	Solid 5-nitrobenzo[d]thiazole-2-thiol (4.0 g, 18.8 mmol) was placed in a round bottom flask and cooled to 0°C while S02CI2(9.1 mL, 1 13 mmol) was slowly added at 0°C. Upon complete additions, the yellow suspension was stirred at 0°C for 5 min, then at rt for 2 h. The mixture was poured onto ice/water (200 mL) and stirred for 1 h. The precipitate that formed was collected, washed with water and dried under high vacuum. The material was slurried in EA (25 mL), vigorously stirred for 15 min and filtered. The filtrate was concentrated and dried. The obtained solid absorbed to silica gel and purified by CC eluting with heptane:EA 4:1 to give the title compound (2.02 g) as a solid; LC-MS: tR= 0.84 min; [M+H]+= 214.51 ;1H NMR (400 MHz, CDCI3) delta: 8.84 (d, J = 2.2 Hz, 1 H), 8.35 (dd, J, = 2.2 Hz, J2= 8.9 Hz, 1 H), 7.98 (d, J = 8.9 Hz, 1 H).

Reference： [1]Journal of Heterocyclic Chemistry,2005,vol. 42,p. 727 - 730
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7661 - 7670
[3]Patent: WO2016/207785,2016,A1 .Location in patent: Page/Page column 45; 46

5
[ 80945-80-8 ]
[ 3622-38-6 ]