[ CAS No. 62473-92-1 ] {[proInfo.proName]}

Name: 62473-92-1|6-Bromobenzo[d]isothiazol-3(2H)-one 1,1-dioxide|98% (contains <1%H2O)
Brand: Ambeed
SKU: A141727
Price: 26.0 USD
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Structure of 62473-92-1 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 62473-92-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 62473-92-1 ]

SDS Specification

Alternatived Products of [ 62473-92-1 ]

Product Details of [ 62473-92-1 ]

CAS No. :	62473-92-1	MDL No. :	MFCD03789731
Formula :	C₇H₄BrNO₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CNDPIUXFHSMKMG-UHFFFAOYSA-N
M.W :	262.08	Pubchem ID :	10540996
Synonyms :

Calculated chemistry of [ 62473-92-1 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	52.42
TPSA :	71.62 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) :	-6.76 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.92
Log Po/w (XLOGP3) :	1.6
Log Po/w (WLOGP) :	1.58
Log Po/w (MLOGP) :	0.74
Log Po/w (SILICOS-IT) :	1.23
Consensus Log Po/w :	1.22

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.81
Solubility :	0.402 mg/ml ; 0.00153 mol/l
Class :	Soluble
Log S (Ali) :	-2.72
Solubility :	0.505 mg/ml ; 0.00193 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.39
Solubility :	0.107 mg/ml ; 0.000407 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.37

Safety of [ 62473-92-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 62473-92-1 ]

* 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 [ 62473-92-1 ]
Downstream synthetic route of [ 62473-92-1 ]

[ 62473-92-1 ] Synthesis Path-Upstream 1~8

1
[ 135484-83-2 ]
[ 62473-92-1 ]

Yield	Reaction Conditions	Operation in experiment
10%	Stage #1: With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.75 h; Stage #2: With sulfur dioxide In water; acetic acid at 0 - 20℃; for 3.5 h; Stage #3: With ammonium hydroxide In water at 10 - 20℃; for 1 h;	Preparation 49 6-Bromo-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one A solution of methyl 2-amino-4-bromobenzoate (4.5 g, 20 mmol) in 20percent hydrochloric acid (30 mL) was stirred until all solids were dissolved. The solution was cooled to 0° C. and a solution of sodium nitrite (1.4 g, 0.020 mol) in water (20 mL) was added dropwise at such a rate that the internal reaction temperature did not exceed 5° C. The mixture was stirred at 0° C. for 45 minutes. Sulfur dioxide was bubbled into a mixture of acetic acid (50 mL) and water (5 mL) at 0° C. until the solution was saturated. Copper (I) chloride (2.0 g, 0.020 mol) was then added to the saturated sulfur dioxide solution. The mixture was cooled to 0° C. To this mixture was added the diazonium salt solution dropwise with vigorous stirring over a period of 30 minutes. The reaction mixture was stirred at 0° C. for 1 hour and then the mixture was allowed to warm to room temperature. The mixture was stirred at room temperature for 2 h before it was poured into ice water (250 mL) and extracted with EtOAc (3*50 mL). The organics were washed with sat. NaHCO₃ solution and dried over anhydrous Na₂SO₄. The solvent was removed in vacuo to afford an oily residue which was dissolved in tetrahydrofuran (40 mL) and cooled to 0° C. To this mixture was added a cold (0° C.) solution of ammonium hydroxide (28percent, 40 mL) portion-wise at such a rate that the internal reaction temperature was maintained below 10° C. The mixture was allowed to warm to room temperature and was then stirred at room temperature for 1 h. The solvent was removed in vacuo and the residue was dissolved in saturated aqueous sodium bicarbonate (40 mL) and washed with diethyl ether (50 mL). The aqueous layer was acidified with concentrated hydrochloric acid to pH 1. The resulting precipitate was collected by filtration and was dried under vacuum to produce of 6-Bromo-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one (500 mg, 10percent yield). ¹H NMR (400 MHz, DMSO) δ 8.44 (d, J=1.5, 1H), 8.04 (dd, J=8.1, 1.5, 1H), 7.81 (d, J=8.0, 1H).
10%	Stage #1: With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.75 h; Stage #2: With sulfur dioxide; copper(l) chloride In water; acetic acid at 0 - 20℃; for 3.5 h;	solution of methyl 2-amino-4-bromobenzoate (4.5 g, 20 mmol) in 20percent hydrochloric acid (30 mL) was stirred until all solids were dissolved. The solution was cooled to 0° C. and a solution of sodium nitrite (1.4 g, 0.020 mol) in water (20 mL) was added dropwise at such a rate that the internal reaction temperature did not exceed 5° C. The mixture was stirred at 0° C. for 45 minutes. Sulfur dioxide was bubbled into a mixture of acetic acid (50 mL) and water (5 mL) at 0° C. until the solution was saturated. Copper (I) chloride (2.0 g, 0.020 mol) was then added to the saturated sulfur dioxide solution. The mixture was cooled to 0° C. To this mixture was added the diazonium salt solution dropwise with vigorous stirring over a period of 30 minutes. The reaction mixture was stirred at 0° C. for 1 hour and then the mixture was allowed to warm to room temperature. The mixture was stirred at room temperature for 2 h before it was poured into ice water (250 mL) and extracted with EtOAc (3*50 mL). The organics were washed with sat. NaHCO₃ solution and dried over anhydrous Na2SO₄. The solvent was removed in vacuo to afford an oily residue which was dissolved in tetrahydrofuran (40 mL) and cooled to 0° C. To this mixture was added a cold (0° C.) solution of ammonium hydroxide (28percent, 40 mL) portion-wise at such a rate that the internal reaction temperature was maintained below 10° C. The mixture was allowed to warm to room temperature and was then stirred at room temperature for 1 h. The solvent was removed in vacuo and the residue was dissolved in saturated aqueous sodium bicarbonate (40 mL) and washed with diethyl ether (50 mL). The aqueous layer was acidified with concentrated hydrochloric acid to pH 1. The resulting precipitate was collected by filtration and was dried under vacuum to produce of 6-Bromo-1,1-dioxo-1,2-dihydro-1λ6-benzo[d]isothiazol-3-one (500 mg, 10percent yield). 1H NMR (400 MHz, DMSO) δ 8.44 (d, J=1.5, 1H), 8.04 (dd, J=8.1, 1.5, 1H), 7.81 (d, J=8.0, 1H).

Reference： [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 4, p. 949 - 961
[2] Patent: US2008/9524, 2008, A1, . Location in patent: Page/Page column 410
[3] Patent: US2015/231142, 2015, A1, . Location in patent: Paragraph 1267

2
[ 56919-16-5 ]
[ 62473-92-1 ]

Reference： [1] Arzneimittel-Forschung/Drug Research, 1996, vol. 46, # 10, p. 966 - 971
[2] Tetrahedron, 2006, vol. 62, # 33, p. 7902 - 7910
[3] Patent: WO2013/131408, 2013, A1,
[4] Patent: WO2010/100139, 2010, A1,

3
[ 135484-83-2 ]
[ 62473-92-1 ]

Yield	Reaction Conditions	Operation in experiment
10%	With ammonium hydroxide; acetic acid; sodium nitrite In tetrahydrofuran; hydrogenchloride; water; sodium hydrogencarbonate	Preparation 49 6-Bromo-1,1-dioxo-1,2-dihydro-1λ6-benzo[d]isothiazol-3-one A solution of methyl 2-amino-4-bromobenzoate (4.5 g, 20 mmol) in 20percent hydrochloric acid (30 mL) was stirred until all solids were dissolved. The solution was cooled to 0° C. and a solution of sodium nitrite (1.4 g, 0.020 mol) in water (20 mL) was added dropwise at such a rate that the internal reaction temperature did not exceed 5° C. The mixture was stirred at 0° C. for 45 minutes. Sulfur dioxide was bubbled into a mixture of acetic acid (50 mL) and water (5 mL) at 0° C. until the solution was saturated. Copper (I) chloride (2.0 g, 0.020 mol) was then added to the saturated sulfur dioxide solution. The mixture was cooled to 0° C. To this mixture was added the diazonium salt solution dropwise with vigorous stirring over a period of 30 minutes. The reaction mixture was stirred at 0° C. for 1 hour and then the mixture was allowed to warm to room temperature. The mixture was stirred at room temperature for 2 h before it was poured into ice water (250 mL) and extracted with EtOAc (3*50 mL). The organics were washed with sat. NaHCO₃ solution and dried over anhydrous Na2SO₄. The solvent was removed in vacuo to afford an oily residue which was dissolved in tetrahydrofuran (40 mL) and cooled to 0° C. To this mixture was added a cold (0° C.) solution of ammonium hydroxide (28percent, 40 mL) portion-wise at such a rate that the internal reaction temperature was maintained below 10° C. The mixture was allowed to warm to room temperature and was then stirred at room temperature for 1 h. The solvent was removed in vacuo and the residue was dissolved in saturated aqueous sodium bicarbonate (40 mL) and washed with diethyl ether (50 mL). The aqueous layer was acidified with concentrated hydrochloric acid to pH 1. The resulting precipitate was collected by filtration and was dried under vacuum to produce of 6-Bromo-1,1-dioxo-1,2-dihydro-1λ6-benzo[d]isothiazol-3-one (500 mg, 10percent yield). 1H NMR (400 MHz, DMSO) δ 8.44 (d, J=1.5, 1H), 8.04 (dd, J=8.1, 1.5, 1H), 7.81 (d, J=8.0, 1H).

Reference： [1] Patent: US2011/98311, 2011, A1,

4
[ 52727-57-8 ]
[ 29632-82-4 ]
[ 62473-92-1 ]

Yield	Reaction Conditions	Operation in experiment
9%	With ammonia; acetic acid; sodium nitrite In tetrahydrofuran; hydrogenchloride; methanol; water; sodium hydrogencarbonate	Step b: 6-Bromo-1,1-dioxo-1,2-dihydro-1λ6-benzo[d]isothiazol-3-one A solution of the methyl 2-amino-5-bromobenzoate (20.0 g, 86.9 mol) in 20percent hydrochloric acid (60 mL) was warmed until all solids were dissolved. The solution was cooled to 0° C. with stirring to precipitate the hydrochloride salt. To this suspension was added a solution of sodium nitrite (6.10 g, 8.84 mol) in water (20 mL) dropwise at such a rate that the internal reaction temperature did not exceed 5° C. The mixture was stirred at 0° C. for 45 minutes to afford a clear solution. Sulfur dioxide was bubbled into a mixture of acetic acid (100 mL) and water (10 mL) at 0° C. Copper (I) chloride (8.6 g, 0.088 mol) was then added to the sulfur dioxide solution. The mixture was then cooled to 0° C. To this mixture was added the diazonium salt solution portion-wise with vigorous stirring over a period of 30 minutes. The reaction mixture was stirred at 0° C. for 1 h and then the mixture was allowed to warm to room temperature. The mixture was stirred at room temperature for 2 h before it was quenched with ice water (500 mL). The mixture was extracted with EtOAc (3*) and the extracts were washed with sat. NaHCO3 and dried over anhydrous Na2SO4. The solvent was removed in vacuo to afford an oily residue. The residue was dissolved in THF (60 mL) and the solution was cooled to 0° C. To this mixture was added a cold (0° C.) solution of sat. NH3 (50 mL) in MeOH portion-wise at such a rate that the internal reaction temperature was maintained below 10° C. After the addition was complete, the mixture was allowed to warm to room temperature and was stirred for 1 h. The solvent was removed in vacuo and the residue was dissolved in saturated aqueous sodium bicarbonate (60 mL) and washed with diethyl ether (80 mL). The aqueous layer was acidified with concentrated HCl to pH to 1. The resulting precipitate was collected by filtration and was dried in vacuo to afford 6-bromo-1,1-dioxo-1,2-dihydro-1λ6-benzo[d]isothiazol-3-one (2.1 g, 9percent yield). 1H NMR (300 MHz, CDCl3) δ 8.18 (d, J=1.8, 1H), 8.03 (dd, J=8.1, 1.8, 1H), 7.79 (d, J=8.1, 1H).

Reference： [1] Patent: US2011/98311, 2011, A1,

5
[ 69321-56-8 ]
[ 62473-92-1 ]

Reference： [1] Arzneimittel-Forschung/Drug Research, 1996, vol. 46, # 10, p. 966 - 971
[2] Patent: WO2013/131408, 2013, A1,

6
[ 106-38-7 ]
[ 62473-92-1 ]

Reference： [1] Patent: WO2013/131408, 2013, A1,

7
[ 5794-88-7 ]
[ 29632-82-4 ]
[ 62473-92-1 ]

Reference： [1] Patent: US2011/98311, 2011, A1,

8
[ 62473-92-1 ]
[ 10026-13-8 ]
[ 154607-01-9 ]

Reference： [1] American Chemical Journal, 1903, vol. 30, p. 508

[ 62473-92-1 ] Synthesis Path-Downstream 1~58

1
[ 62473-92-1 ]
sodium 6-bromo-1,2-benzisothiazol-3(2H)-one 1,1-dioxide [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971

2
[ 56919-16-5 ]
[ 62473-92-1 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971
[2]Tetrahedron,2006,vol. 62,p. 7902 - 7910
[3]Patent: WO2013/131408,2013,A1
[4]Patent: WO2010/100139,2010,A1

4
4-bromo-2-sulfamide-benzonitrile [ No CAS ]
[ 62473-92-1 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1895,vol. 286,p. 386

5
4-bromo-benzoic acid sulfonic acid-⁽²⁾-dichloride [ No CAS ]
[ 62473-92-1 ]

Reference： [1]American Chemical Journal,1903,vol. 30,p. 508

6
4-bromo-toluene-sulfonic acid-⁽²⁾-amide [ No CAS ]
[ 62473-92-1 ]

Reference： [1]American Chemical Journal,1886,vol. 8,p. 233

7
[ 62473-92-1 ]
[ 10026-13-8 ]
[ 154607-01-9 ]

Reference： [1]American Chemical Journal,1903,vol. 30,p. 508

8
[ 62473-92-1 ]
5-bromo-2-cyanobenzenesulfonyl chloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 949 - 961

9
[ 135484-83-2 ]
[ 62473-92-1 ]

Yield	Reaction Conditions	Operation in experiment
10%		Preparation 49 6-Bromo-1,1-dioxo-1,2-dihydro-1lambda6-benzo[d]isothiazol-3-one A solution of methyl 2-amino-4-bromobenzoate (4.5 g, 20 mmol) in 20percent hydrochloric acid (30 mL) was stirred until all solids were dissolved. The solution was cooled to 0° C. and a solution of sodium nitrite (1.4 g, 0.020 mol) in water (20 mL) was added dropwise at such a rate that the internal reaction temperature did not exceed 5° C. The mixture was stirred at 0° C. for 45 minutes. Sulfur dioxide was bubbled into a mixture of acetic acid (50 mL) and water (5 mL) at 0° C. until the solution was saturated. Copper (I) chloride (2.0 g, 0.020 mol) was then added to the saturated sulfur dioxide solution. The mixture was cooled to 0° C. To this mixture was added the diazonium salt solution dropwise with vigorous stirring over a period of 30 minutes. The reaction mixture was stirred at 0° C. for 1 hour and then the mixture was allowed to warm to room temperature. The mixture was stirred at room temperature for 2 h before it was poured into ice water (250 mL) and extracted with EtOAc (3*50 mL). The organics were washed with sat. NaHCO3 solution and dried over anhydrous Na2SO4. The solvent was removed in vacuo to afford an oily residue which was dissolved in tetrahydrofuran (40 mL) and cooled to 0° C. To this mixture was added a cold (0° C.) solution of ammonium hydroxide (28percent, 40 mL) portion-wise at such a rate that the internal reaction temperature was maintained below 10° C. The mixture was allowed to warm to room temperature and was then stirred at room temperature for 1 h. The solvent was removed in vacuo and the residue was dissolved in saturated aqueous sodium bicarbonate (40 mL) and washed with diethyl ether (50 mL). The aqueous layer was acidified with concentrated hydrochloric acid to pH 1. The resulting precipitate was collected by filtration and was dried under vacuum to produce of 6-Bromo-1,1-dioxo-1,2-dihydro-1lambda6-benzo[d]isothiazol-3-one (500 mg, 10percent yield). 1H NMR (400 MHz, DMSO) delta 8.44 (d, J=1.5, 1H), 8.04 (dd, J=8.1, 1.5, 1H), 7.81 (d, J=8.0, 1H).
10%		solution of methyl 2-amino-4-bromobenzoate (4.5 g, 20 mmol) in 20percent hydrochloric acid (30 mL) was stirred until all solids were dissolved. The solution was cooled to 0° C. and a solution of sodium nitrite (1.4 g, 0.020 mol) in water (20 mL) was added dropwise at such a rate that the internal reaction temperature did not exceed 5° C. The mixture was stirred at 0° C. for 45 minutes. Sulfur dioxide was bubbled into a mixture of acetic acid (50 mL) and water (5 mL) at 0° C. until the solution was saturated. Copper (I) chloride (2.0 g, 0.020 mol) was then added to the saturated sulfur dioxide solution. The mixture was cooled to 0° C. To this mixture was added the diazonium salt solution dropwise with vigorous stirring over a period of 30 minutes. The reaction mixture was stirred at 0° C. for 1 hour and then the mixture was allowed to warm to room temperature. The mixture was stirred at room temperature for 2 h before it was poured into ice water (250 mL) and extracted with EtOAc (3*50 mL). The organics were washed with sat. NaHCO3 solution and dried over anhydrous Na2SO4. The solvent was removed in vacuo to afford an oily residue which was dissolved in tetrahydrofuran (40 mL) and cooled to 0° C. To this mixture was added a cold (0° C.) solution of ammonium hydroxide (28percent, 40 mL) portion-wise at such a rate that the internal reaction temperature was maintained below 10° C. The mixture was allowed to warm to room temperature and was then stirred at room temperature for 1 h. The solvent was removed in vacuo and the residue was dissolved in saturated aqueous sodium bicarbonate (40 mL) and washed with diethyl ether (50 mL). The aqueous layer was acidified with concentrated hydrochloric acid to pH 1. The resulting precipitate was collected by filtration and was dried under vacuum to produce of 6-Bromo-1,1-dioxo-1,2-dihydro-1lambda6-benzo[d]isothiazol-3-one (500 mg, 10percent yield). 1H NMR (400 MHz, DMSO) delta 8.44 (d, J=1.5, 1H), 8.04 (dd, J=8.1, 1.5, 1H), 7.81 (d, J=8.0, 1H).

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 949 - 961
[2]Patent: US2008/9524,2008,A1 .Location in patent: Page/Page column 410
[3]Patent: US2015/231142,2015,A1 .Location in patent: Paragraph 1267

10
[ 1000693-05-9 ]
[ 62473-92-1 ]
[ 1000692-98-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 120℃; for 0.166667h;Microwave irradiation;	Preparation 54 1-(2,2-Difluoro-2H-1,3-benzodioxol-5-yl)-N-[4-methyl-3-(1,1,3-trioxo-2,3-dihydro-1lambda6,2-benzothiazol-6-yl)phenyl]cyclopropane-1-carboxamide 1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropanecarboxamide (46 mg, 0.10 mmol), 6-bromo-1,1-dioxo-1,2-dihydro-1lambda6-benzo[d]isothiazol-3-one (26 mg, 0.10 mmol), Pd(dppf)Cl2 (4.0 mg, 0.0050 mmol), 2M Na2CO3 (150 muL, 0.30 mmol), and DMF (1 mL) were combined and heated at 120° C. in the microwave for 10 min. The mixture was filtered and purified by reverse phase preparatory HPLC to give 1-(2,2-difluoro-2H-1,3-benzodioxol-5-yl)-N-[4-methyl-3-(1,1,3-trioxo-2,3-dihydro-1lambda6,2-benzothiazol-6-yl)phenyl]cyclopropane-1-carboxamide. ESI-MS m/z calc. 512.5, found 513.5 (M+1)+. Retention time 1.93 minutes.

Reference： [1]Patent: US2008/9524,2008,A1 .Location in patent: Page/Page column 413

11
[ 62473-92-1 ]
[ 612537-88-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 949 - 961

12
[ 62473-92-1 ]
5-bromo-2-cyano-N-(5-isopropyl-3,4-dimethyl-1,3-thiazol-2(3H)-ylidene)benzenesulfonamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 949 - 961

13
[ 62473-92-1 ]
[ 524707-34-4 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971

14
[ 62473-92-1 ]
[ 183859-50-9 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971

15
[ 62473-92-1 ]
[ 183859-73-6 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971

16
[ 62473-92-1 ]
7-Bromo-4-hydroxy-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazine-3-carboxylic acid (3-methyl-4-oxo-2-thioxo-imidazolidin-1-yl)-amide [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971

17
[ 62473-92-1 ]
7-Bromo-4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazine-3-carboxylic acid (3-methyl-4-oxo-2-thioxo-imidazolidin-1-yl)-amide [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971

18
[ 62473-92-1 ]
7-Bromo-4-hydroxy-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazine-3-carboxylic acid (3-allyl-4-oxo-2-thioxo-imidazolidin-1-yl)-amide [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971

19
[ 62473-92-1 ]
7-Bromo-4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazine-3-carboxylic acid (3-allyl-4-oxo-2-thioxo-imidazolidin-1-yl)-amide [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971

20
[ 62473-92-1 ]
7-Bromo-4-hydroxy-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazine-3-carboxylic acid (4-oxo-3-phenyl-2-thioxo-imidazolidin-1-yl)-amide [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971

21
[ 62473-92-1 ]
7-Bromo-4-hydroxy-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazine-3-carboxylic acid (3-benzyl-4-oxo-2-thioxo-imidazolidin-1-yl)-amide [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971

22
[ 62473-92-1 ]
7-Bromo-4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazine-3-carboxylic acid (4-oxo-3-phenyl-2-thioxo-imidazolidin-1-yl)-amide [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971

23
[ 62473-92-1 ]
7-Bromo-4-hydroxy-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazine-3-carboxylic acid [3-(4-chloro-phenyl)-4-oxo-2-thioxo-imidazolidin-1-yl]-amide [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971

24
[ 62473-92-1 ]
7-Bromo-4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazine-3-carboxylic acid (3-benzyl-4-oxo-2-thioxo-imidazolidin-1-yl)-amide [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971

25
[ 62473-92-1 ]
7-Bromo-4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazine-3-carboxylic acid [3-(4-chloro-phenyl)-4-oxo-2-thioxo-imidazolidin-1-yl]-amide [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971

26
[ 106-38-7 ]
potassium-<2-amino-4-methyl benzoate> [ No CAS ]
[ 62473-92-1 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971

27
[ 69321-56-8 ]
[ 62473-92-1 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1996,vol. 46,p. 966 - 971
[2]Patent: WO2013/131408,2013,A1

28
[ 62473-92-1 ]
[ 87476-69-5 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentachloride; trichlorophosphate; at 160℃; for 16h;	B. [1, 1-DIOXO-6-(3-TRIFLUOROMETHYL-PHENYL)1H-?6-BENZO[D]ISOTHIAZO-3-YL]-(4- TERT-BUTYL-PHENYL)-AMINE 1. 6-bromo-3-chloro-benzo[d]isothiazole 1,1-dioxide Heat a mixture of 6-bromo-1, 1-dioxo-1, 2-DIHYDRO-1 ? 6-benzo [d] isothiazol-3-one (Kwon et al. (1996) Arzneim. FORSCH. 46 (10): 966-971 ; 1.5 MMOL), POC13 (3 ml) and PCIS (2.0 mmol) for 16 hours at 160°C. Quench with ice, extract with EtOAc, and concentrate to give 6-bromo-3-chloro-benzo [d] isothiazole 1, 1-dioxide.

Reference： [1]Patent: WO2005/9982,2005,A2 .Location in patent: Page/Page column 43

29
[ 62473-92-1 ]
[ 3395-91-3 ]
methyl 3-(3-bromosaccharinyl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In N,N-dimethyl-formamide; at 20 - 130℃; for 6h;	To a 100-mL round-bottomed flask containing 3-bromosaccharin (1.0 g, 3.8 mmol,Synthelee) in DMF (5 mL), was slowly added NaH (0.15 g, 3.8 mmol, 60percent in mineral oil, Aldrich) at room temp. Methyl 3-bromo-propanoate (2.1 mL, 19 mmol, Aldrich) was added and the reaction mixture was refluxed at 130 °C for 6 h. The reaction was quenched with water (15 mL) and the compound was extracted with EtOAc (2x20 mL). The organic phase was washed with 5percent brine (2x 10 mL), dried over Na2SO4, filtered, and concentrated. Purification EPO <DP n="124"/>with column chromatography over silica gel with hexane:EtOAc:MeOH (5:5:1) gave the title compound.

Reference： [1]Patent: WO2006/36664,2006,A1 .Location in patent: Page/Page column 122-123

30
[ 73278-98-5 ]
[ 62473-92-1 ]
N-[3-[3-[(1-piperidinyl)methyl]phenoxy]propyl]-6-bromo-1,2-benzisothiazol-3-amine 1,1-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentachloride; In 6-bromo-3-chlorobenzo[d]isothiazole 1,1-dioxide; 1,2-dichloro-benzene; acetonitrile;	EXAMPLE 14 N-[3-[3-[(1-piperidinyl)methyl]phenoxy]propyl]-6-bromo-1,2-benzisothiazol-3-amine 1,1-dioxide, hydrochloride A mixture of 4.00 g (15 mmol) <strong>[62473-92-1]6-bromo-1,2-benzisothiazol-3(2H)-one 1,1-dioxide</strong> and 3.57 g (17 mmol) phosphorus pentachloride in 5 ml o-dichlorobenzene is heated from ambient temperature to 160° C. over one hour and is held at that temperature for one additional hour. Upon cooling, liquids are removed in vacuo and the residual 6-bromo-3-chlorobenzisothiazole 1,1-dioxide is suspended in acetonitrile and added portionwise to a solution of 3.7 g (15 mmol) 3-[3-[(1-piperidinyl)methyl]phenoxy]propylamine in refluxing acetonitrile. Heating at reflux is continued for one hour after completion of the addition, after which the reaction mixture is cooled to room temperature. The solution is decanted away from a small quantity of gum and the solvent is removed on a rotoevaporator. The resulting oil is dissolved in absolute ethanol, from which the title compound precipitates. m.p. 217°-220° C. IR (KBr) 1625, 1290, 1165, 1150 cm-1

Reference： [1]Patent: US4490527,1984,A

31
[ 62473-92-1 ]
[ 2969-81-5 ]
[ 1242317-11-8 ]

Reference： [1]Synthetic Communications,2010,vol. 40,p. 2464 - 2474

32
[ 62473-92-1 ]
[ 14660-52-7 ]
[ 1242317-12-9 ]

Reference： [1]Synthetic Communications,2010,vol. 40,p. 2464 - 2474

33
4-bromo-2-sulfamoylbenzoic acid [ No CAS ]
[ 62473-92-1 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sulfuric acid; at 20℃; for 3h;	The compound 150A (1.59 g, 5.56 mmol) is dissolved in 6 mL of concentrated sulfuric acid at room temperature and the reaction medium is stirred for 3 hours before being poured over ice. The suspension is filtered. The precipitate is rinsed three times with water, and then dried for 24 hours at 500C and in vacuo. The compound 150B (1.33 g, 89percent) is obtained as a white solid.HPLC: RT = 3.16 min, 96percent1H NMR, dmso-de, delta (ppm) : 7.85 (d, IH); 8.08 (d, IH); 8.48 (s, IH) . Mass spectrum (ESI-) : m/z 260 (M-H", 100percent); 262 (M-H", 94percent) .

Reference： [1]Patent: WO2010/100139,2010,A1 .Location in patent: Page/Page column 105-106
[2]Patent: WO2013/131408,2013,A1 .Location in patent: Page/Page column 87

34
[ 62473-92-1 ]
[ 75-16-1 ]
[ 1303975-97-4 ]

Reference： [1]Synlett,2011,p. 402 - 404

35
copper (I) chloride [ No CAS ]
[ 135484-83-2 ]
[ 62473-92-1 ]

Yield	Reaction Conditions	Operation in experiment
10%	With ammonium hydroxide; acetic acid; sodium nitrite; In tetrahydrofuran; hydrogenchloride; water; sodium hydrogencarbonate;	Preparation 496-Bromo-1,1-dioxo-1,2-dihydro-1lambda6-benzo[d]isothiazol-3-oneA solution of methyl 2-amino-4-bromobenzoate (4.5 g, 20 mmol) in 20percent hydrochloric acid (30 mL) was stirred until all solids were dissolved.The solution was cooled to 0° C. and a solution of sodium nitrite (1.4 g, 0.020 mol) in water (20 mL) was added dropwise at such a rate that the internal reaction temperature did not exceed 5° C.The mixture was stirred at 0° C. for 45 minutes.Sulfur dioxide was bubbled into a mixture of acetic acid (50 mL) and water (5 mL) at 0° C. until the solution was saturated.Copper (I) chloride (2.0 g, 0.020 mol) was then added to the saturated sulfur dioxide solution.The mixture was cooled to 0° C.To this mixture was added the diazonium salt solution dropwise with vigorous stirring over a period of 30 minutes.The reaction mixture was stirred at 0° C. for 1 hour and then the mixture was allowed to warm to room temperature.The mixture was stirred at room temperature for 2 h before it was poured into ice water (250 mL) and extracted with EtOAc (3*50 mL).The organics were washed with sat.NaHCO3 solution and dried over anhydrous Na2SO4.The solvent was removed in vacuo to afford an oily residue which was dissolved in tetrahydrofuran (40 mL) and cooled to 0° C.To this mixture was added a cold (0° C.) solution of ammonium hydroxide (28percent, 40 mL) portion-wise at such a rate that the internal reaction temperature was maintained below 10° C.The mixture was allowed to warm to room temperature and was then stirred at room temperature for 1 h.The solvent was removed in vacuo and the residue was dissolved in saturated aqueous sodium bicarbonate (40 mL) and washed with diethyl ether (50 mL).The aqueous layer was acidified with concentrated hydrochloric acid to pH 1.The resulting precipitate was collected by filtration and was dried under vacuum to produce of 6-Bromo-1,1-dioxo-1,2-dihydro-1lambda6-benzo[d]isothiazol-3-one (500 mg, 10percent yield).1H NMR (400 MHz, DMSO) delta 8.44 (d, J=1.5, 1H), 8.04 (dd, J=8.1, 1.5, 1H), 7.81 (d, J=8.0, 1H).

Reference： [1]Patent: US2011/98311,2011,A1

36
copper (I) chloride [ No CAS ]
[ 52727-57-8 ]
[ 29632-82-4 ]
[ 62473-92-1 ]

Yield	Reaction Conditions	Operation in experiment
9%	With ammonia; acetic acid; sodium nitrite; In tetrahydrofuran; hydrogenchloride; methanol; water; sodium hydrogencarbonate;	Step b:6-Bromo-1,1-dioxo-1,2-dihydro-1lambda6-benzo[d]isothiazol-3-oneA solution of the methyl 2-amino-5-bromobenzoate (20.0 g, 86.9 mol) in 20percent hydrochloric acid (60 mL) was warmed until all solids were dissolved.The solution was cooled to 0° C. with stirring to precipitate the hydrochloride salt.To this suspension was added a solution of sodium nitrite (6.10 g, 8.84 mol) in water (20 mL) dropwise at such a rate that the internal reaction temperature did not exceed 5° C.The mixture was stirred at 0° C. for 45 minutes to afford a clear solution.Sulfur dioxide was bubbled into a mixture of acetic acid (100 mL) and water (10 mL) at 0° C. Copper (I) chloride (8.6 g, 0.088 mol) was then added to the sulfur dioxide solution.The mixture was then cooled to 0° C.To this mixture was added the diazonium salt solution portion-wise with vigorous stirring over a period of 30 minutes.The reaction mixture was stirred at 0° C. for 1 h and then the mixture was allowed to warm to room temperature.The mixture was stirred at room temperature for 2 h before it was quenched with ice water (500 mL).The mixture was extracted with EtOAc (3*) and the extracts were washed with sat.NaHCO3 and dried over anhydrous Na2SO4.The solvent was removed in vacuo to afford an oily residue.The residue was dissolved in THF (60 mL) and the solution was cooled to 0° C.To this mixture was added a cold (0° C.) solution of sat. NH3 (50 mL) in MeOH portion-wise at such a rate that the internal reaction temperature was maintained below 10° C.After the addition was complete, the mixture was allowed to warm to room temperature and was stirred for 1 h.The solvent was removed in vacuo and the residue was dissolved in saturated aqueous sodium bicarbonate (60 mL) and washed with diethyl ether (80 mL).The aqueous layer was acidified with concentrated HCl to pH to 1.The resulting precipitate was collected by filtration and was dried in vacuo to afford 6-bromo-1,1-dioxo-1,2-dihydro-1lambda6-benzo[d]isothiazol-3-one (2.1 g, 9percent yield).1H NMR (300 MHz, CDCl3) delta 8.18 (d, J=1.8, 1H), 8.03 (dd, J=8.1, 1.8, 1H), 7.79 (d, J=8.1, 1H).

Reference： [1]Patent: US2011/98311,2011,A1

37
[ 74-96-4 ]
[ 62473-92-1 ]
N-ethyl-6-bromosaccharin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; sodium iodide; In N,N-dimethyl-formamide; at 100℃; for 1h;	The first step of the synthesis of (16), the preparation of 6-bromo saccharin (6-bromo-1 ,1 - dioxo-1 ,2-benzothiazol-3-one) (17) is done according to Bioorg. Med. Chem. 13 (2005), 949-961 .In the second step, 6-bromo saccharin is alkylated according to the following procedure: 60.5 g of <strong>[62473-92-1]6-bromosaccharin</strong> (17) are brought into 260 ml of dimethylformamide. After the addition of 74.8 g of bromoethane, 32.0 g of potassium carbonate and 2.6 g of sodium iodide, the mixture is heated to 100 °C for one hour. After cooling down to roomtemperature, the mixture is given into 1 .5 I of water. Thereafter the reaction flask is washed twice with 100 ml water. The combined aqueous mixtures are filtered off and the filtered solid is given into 730 ml of water. After stirring for half an hour, it is filtered again. The compound is dried in vacuum.Yield: 54 g of N-ethyl-<strong>[62473-92-1]6-bromosaccharin</strong> (18)

Reference： [1]Patent: WO2011/72966,2011,A1 .Location in patent: Page/Page column 14

38
[ 62473-92-1 ]
[ 1310720-04-7 ]

Reference： [1]Patent: WO2011/72966,2011,A1

39
[ 62473-92-1 ]
[ 1310720-02-5 ]

Reference： [1]Patent: WO2011/72966,2011,A1

40
[ 62473-92-1 ]
[ 1310719-66-4 ]

Reference： [1]Patent: WO2011/72966,2011,A1

41
[ 62473-92-1 ]
[ 1310719-85-7 ]

Reference： [1]Patent: WO2011/72966,2011,A1

42
[ 62473-92-1 ]
[ 1414888-02-0 ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2012,vol. 67,p. 1070 - 1080,11
[2]Zeitschrift fur Naturforschung, B: Chemical Sciences,2012,vol. 67,p. 1070 - 1080

43
[ 62473-92-1 ]
[ 1414888-03-1 ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2012,vol. 67,p. 1070 - 1080,11
[2]Zeitschrift fur Naturforschung, B: Chemical Sciences,2012,vol. 67,p. 1070 - 1080

44
[ 62473-92-1 ]
[ 1414888-04-2 ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2012,vol. 67,p. 1070 - 1080,11
[2]Zeitschrift fur Naturforschung, B: Chemical Sciences,2012,vol. 67,p. 1070 - 1080,11
[3]Zeitschrift fur Naturforschung, B: Chemical Sciences,2012,vol. 67,p. 1070 - 1080
[4]Zeitschrift fur Naturforschung, B: Chemical Sciences,2012,vol. 67,p. 1070 - 1080

45
[ 62473-92-1 ]
[ 1414887-99-2 ]

46
[ 62473-92-1 ]
[ 100-39-0 ]
[ 1414888-01-9 ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2012,vol. 67,p. 1070 - 1080,11

47
[ 62473-92-1 ]
[ 1341040-15-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; at -8℃; for 2.42h;Reflux;	To R8 (4.5 g, 17.2 mmol) in anhydrous THF (130 mL) is added NaBH4 (6.8 g, 179 mmol) and the reaction mixture is cooled to -8 °C. Boron trifluoride diethyl etherate (25 mL, 197 mmol) is added dropwise over a period of 15 minutes. After 10 additional minutes at -8°C, the reaction mixture is heated at reflux for 2 hours, then cooled to room temperature and ice water (30 mL) is added. 6M NaOH solution is added until th pH is basic and the solution is extracted with ethyl acetate. The organic solution was extracted 3 times with NaOH solution. To the combined and cooled aqueous layers are added 6M HCl solution until the pH is acidic. The aqueous layer is extracted 3 times with ethyl acetate, the combined organic layers are washed with brine, dried and concentrated. The crude product is carried on. m/z 246/148 [M+H]+, rt 0.76 mi LC-MS Method b.
	With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; at -8℃; for 2.41667h;Reflux;	To R8 (4.5 g, 17.2 mmol) in anhydrous THF (130 mL) is added NaBH4 (6.8 g, 179 mmol) and the reaction mixture is cooled to -8° C. Boron trifluoride diethyl etherate (25 mL, 197 mmol) is added dropwise over a period of 15 minutes. After 10 additional minutes at -8° C., the reaction mixture is heated at reflux for 2 hours, then cooled to room temperature and ice water (30 mL) is added. 6M NaOH solution is added until the pH is basic and the solution is extracted with ethyl acetate. The organic solution was extracted 3 times with NaOH solution. To the combined and cooled aqueous layers are added 6M HCl solution until the pH is acidic. The aqueous layer is extracted 3 times with ethyl acetate, the combined organic layers are washed with brine, dried and concentrated. The crude product is carried on. m/z 246/148 [M+H]+, rt 0.76 min, LC-MS Method b.

Reference： [1]Patent: WO2013/41497,2013,A1 .Location in patent: Page/Page column 42
[2]Patent: US2013/172327,2013,A1 .Location in patent: Paragraph 0203; 0204

48
[ 106-38-7 ]
[ 62473-92-1 ]

Reference： [1]Patent: WO2013/131408,2013,A1

49
[ 62473-92-1 ]
[ 76513-69-4 ]
[ 1455471-84-7 ]

Reference： [1]Patent: WO2013/131408,2013,A1 .Location in patent: Page/Page column 87

50
[ 62473-92-1 ]
[ 1455471-86-9 ]

Reference： [1]Patent: WO2013/131408,2013,A1

51
[ 62473-92-1 ]
[ 1455471-85-8 ]

Reference： [1]Patent: WO2013/131408,2013,A1

52
[ 58895-73-1 ]
[ 62473-92-1 ]
[ 1569309-95-0 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 7136 - 7140

53
[ 62473-92-1 ]
[ 824-94-2 ]
6-bromo-2-(4-methoxybenzyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		[0694] To asuspensionof60percentNaH (10.1 mg, 0.254mmol)in DMF (1 mL), <strong>[62473-92-1]6-bromobenzo[d]isothiazol-3(2H)-one 1,1-dioxide</strong> (55.4 mg, 0.212 mmol) was added portionwise at ooC. The resulting mixture was stirred at rt for 15 min andp-methoxy benzyl chloride (27 .6 f.LL, 0.212 mmol) was addeddropwise. The reaction mixture was heated to 70° C. overnight, allowed to cool tort, and treated with water (20 mL).The aqueous layer was extracted with EtOAc (3x50 mL) andthe combined organic layers were dried over Na2S04 , filtered, and concentrated. The resulting solid was re-crystallized from hexane/DCM to obtain compound 38a. 1 H-NMR(400MHz, CDCI 3 ) o(ppm): 8.08 (d, 1=1.5 Hz, lH), 7.89 (dd,1=8.2, 1.6 Hz, lH), 7.69 (d, 1=8.3 Hz, lH), 7.35 (d, 1=8.6 Hz,2H), 6.79 (d, 1=8.6 Hz, 2H), 4.76 (s, 2H), 3.71 (s, 3H).

Reference： [1]Patent: US2014/364414,2014,A1 .Location in patent: Paragraph 0692-0694

54
[ 5794-88-7 ]
[ 29632-82-4 ]
[ 62473-92-1 ]

Reference： [1]Patent: US2011/98311,2011,A1

55
[ 1000693-05-9 ]
[ 62473-92-1 ]
1-(2,2-difluoro-2H-1,3-benzodioxol-5-yl)-N-[4-methyl-3-(1,1,3-trioxo-2,3-dihydro-1λ6,2-benzothiazol-6-yl)phenyl]cyclopropane-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In N,N-dimethyl-formamide; at 120℃; for 0.166667h;Microwave irradiation;	Preparation 54 1-(2,2-Difluoro-2H-1,3-benzodioxol-5-yl)-N-[4-methyl-3-(1,1,3-trioxo-2,3-dihydro-1lambda6,2-benzothiazol-6-yl)phenyl]cyclopropane-1-carboxamide 1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropanecarboxamide (46 mg, 0.10 mmol), 6-bromo-1,1-dioxo-1,2-dihydro-1lambda6-benzo[d]isothiazol-3-one (26 mg, 0.10 mmol), Pd(dppf)Cl2 (4.0 mg, 0.0050 mmol), 2M Na2CO3 (150 muL, 0.30 mmol), and DMF (1 mL) were combined and heated at 120° C. in the microwave for 10 min. The mixture was filtered and purified by reverse phase preparatory HPLC to give 1-(2,2-difluoro-2H-1,3-benzodioxol-5-yl)-N-[4-methyl-3-(1,1,3-trioxo-2,3-dihydro-1lambda6,2-benzothiazol-6-yl)phenyl]cyclopropane-1-carboxamide. ESI-MS m/z calc. 512.5. found 513.5 (M+1)+. Retention time 1.93 minutes.

Reference： [1]Patent: US2015/231142,2015,A1 .Location in patent: Paragraph 1278

56
[ 62473-92-1 ]
[ 98-80-6 ]
1,1-dioxo-6-phenyl-1,2-benzothiazol-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 120℃; for 0.166667h;Microwave irradiation;	Step A : 1 , 1 -dioxo-6-phen l-1 ,2-benzothiazol-3-one PdCI2(dppf) (77.90 mg; 0.10 mmol; 0.05 eq.) and phenylboric acid (279.14 mg; 2.29 mmol; 1.20 eq.) were added to a solution of 6-bromo-1 ,1-dioxo-1 ,2-benzothiazol-3-one (500.00 mg; 1.91 mmol; 1.00 eq.) in ethylene glycol dimethyl ether (5.00 ml). A solution of K2C03 (395.50 mg; 2.86 mmol; 1.50 eq.) in water (1.67 ml) was added and the reaction was stirred 10 minutes at 120°C under microwave irradiation. The mixture was then filtered over Whatmann and the filtrate concentrated under reduced pressure. Water was added to the residue and the resulting aqueous phase was washed twice with EtOAc. Then, the aqueous phase was acidified with HCI 1 N and extracted twice with EtOAc. Organic layers were combined, dried over MgS04, filtered and concentrated under reduced pressure to give 1 ,1-dioxo-6-phenyl-1 ,2-benzothiazol-3-one (409.0 mg ; 83 percent) as an orange powder. H NMR (DMSO-d6, 300MHz): delta 8.25 (m, 2H) ; 8.19 (m, 1 H) ; 7.83 (m, 2H) ; 7.52 (m, 3H).

Reference： [1]Patent: WO2017/64277,2017,A1 .Location in patent: Page/Page column 53-54

57
[ 62473-92-1 ]
[ 823-96-1 ]
[ 4554-06-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,2-dimethoxyethane; water; at 120℃; for 0.25h;Inert atmosphere; Microwave irradiation;	Ste A : 6-methyl-1 , 1-dioxo-1 ,2-benzothiazol-3-one PdCI2(dppf).DCM complex (38.9 mg; 0.05 mmol; 0.05 eq.) and trimethylboroxine (199 muIota1.43 mmol; 1.5 eq.) were added to a solution of <strong>[62473-92-1]6-bromosaccharin</strong>e (250.0 mg; 0.95 mmol; 1 eq.) in ethylene glycol dimethyl ether (2.5 ml_) under Argon. A solution of K2C03 (197.8 mg; 1.43 mmol; 1.50 eq.) in water (1 ml_) was then added and the reaction was stirred 15 minutes at 120C under MW irradiation. The mixture was filtered over Whatman. The filtrate was concentrated under reduced pressure. Water was added and the mixture was extracted twice with EtOAc. Then aqueous layer was acidified with HCI 1 N and extracted twice with EtOAc. Organic layers were combined, dried over MgS04, filtered and concentrated under reduced pressure to give 6-methyl-1 ,1-dioxo-1 ,2- benzothiazol-3-one (156.0 mg; 79 %) as a pale yellow powder, used directly in the next step without further purification. 1H NMR (DMSO-d6, 300 MHz): delta 8.03 (d, J = 7.8 Hz, 1 H) ; 7.82 (d, J = 0.6 Hz, 1 H) ; 7.79 (dd, J = 0.6 Hz, J = 7.5 Hz, 1 H) ; 2.50 (s, 3H).

Reference： [1]Patent: WO2017/64277,2017,A1 .Location in patent: Page/Page column 47

58
[ 62473-92-1 ]
[1,1-dioxo-6-(2-trifluoromethylphenyl)benzo[d]isothiazol-3-yl]-(4-tert-butylphenyl)amine [ No CAS ]

Reference： [1]Patent: WO2005/9982,2005,A2

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 62473-92-1 ] {[proInfo.proName]}

Quality Control of [ 62473-92-1 ]

Related Doc. of [ 62473-92-1 ]

Product Details of [ 62473-92-1 ]

Calculated chemistry of [ 62473-92-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 62473-92-1 ]

Application In Synthesis of [ 62473-92-1 ]

[ 62473-92-1 ] Synthesis Path-Upstream 1~8

[ 62473-92-1 ] Synthesis Path-Downstream 1~58

Related Functional Groups of [ 62473-92-1 ]

Bromides

Amides

Sulfamides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 62473-92-1 ]