[ CAS No. 437652-07-8 ] {[proInfo.proName]}

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Quality Control of [ 437652-07-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 437652-07-8 ]

Product Details of [ 437652-07-8 ]

CAS No. :	437652-07-8	MDL No. :	MFCD16660182
Formula :	C₁₃H₁₇NO₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	267.34	Pubchem ID :	-
Synonyms :

Safety of [ 437652-07-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 437652-07-8 ]

* 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.

Downstream synthetic route of [ 437652-07-8 ]

[ 437652-07-8 ] Synthesis Path-Downstream 1~3

1
[ 141645-88-7 ]
[ 437652-07-8 ]
[ 141625-93-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With iron(III) chloride In dichloromethane for 2h; Heating / reflux;	3 Dronedarone hydrochloride EXAMPLE 3 Dronedarone hydrochloride A mixture of 8 g of 2-butyl-5-(methanesulfonamido)benzofuran, 11.9 g of 4-[3-(dibutylamino)propoxy]benzoyl chloride hydrochloride and 24 ml of dichloromethane is first of all prepared. This mixture is then introduced into a medium consisting of 11.9 g of ferric chloride and 24 ml of dichloromethane. The reaction medium is heated under reflux for 2 hours and cooled to 20° C. 40 ml of water are added and the medium is separated by settling. In this manner, dronedarone hydrochloride is obtained in crude form. Chemical yield: 90%.
90%	In dichloromethane at 25℃; for 2h;	5.1 A mixture of 10 kg of 2-butyl-5-(methanesulfonamido)benzofuran, 13 kg of 4-[3-(dibutylamino)propoxy]benzoyl hydrochloride and 70 1 of dichloromethane is first of all prepared. 19.9 kg of aluminum chloride are then introduced into this mixture (4 molar equivalents of Lewis acid are thus used; 2.5 molar equivalents of ferric chloride were used for the above Example 3). The medium is stirred at 25 C. for two hours. This medium is added to 60 l of water and the medium is separated by settling.
	Stage #1: 4-[3-(di-n-butylamino)-propoxy]-benzoic acid chloride hydrochloride; N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide With aluminum (III) chloride; tin(IV) chloride In dichloromethane at 20℃; for 3h; Stage #2: With hydrogenchloride	9; 10 N - [(2-butyl-2,3-dihydro-5-benzofuranyl) methanesulfonamide(2.40 g, 9 mmol), prepared as described above4- [3- (dibutylamino)] propoxy) benzoyl chloride (10 mmol) was dissolved in 30 ml of dichloromethane,Tin tetrachloride (30 mmol, 3.6 ml)And aluminum trichloride (10mmol) in a mixture of the system slowly dropping into the solution,The reaction was carried out at room temperature for 3 h.The water was slowly added dropwise to the solution under ice-water bath. The reaction was quenched, extracted three times with dichloromethane, and the organic phase was washed with saturated sodium bicarbonate solution and dried. The solvent was evaporated and the pure product was obtained by column chromatography in a yield of 89%. The resulting pure product of N- [2-butyl-3- [4- [3 - (dibutylamino) propoxy] benzoyl] -5-benzofuranyl] -methanesulfonamide was dissolved in ethyl acetate solution , Hydrogen chloride gas was introduced,Until no solid is produced, and the solvent is distilled off to give a white colorN- [2-butyl-3- [4- [3- (dibutylamino) propoxy] benzoyl] -5-benzofuranyl] -methanesulfonamide hydrochloride.

Reference： [1]Current Patent Assignee: SANOFI - US2004/48921, 2004, A1 Location in patent: Page/Page column 4
[2]Current Patent Assignee: SANOFI - US2004/48921, 2004, A1 Location in patent: Page/Page column 5
[3]Current Patent Assignee: YANAN BICON PHARMACEUTICAL LISTED COMPANY - CN103450124, 2016, B Location in patent: Paragraph 0092-0097

2
[ 437652-07-8 ]
[ 141626-36-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: iron(III) chloride / dichloromethane / 5 - 45 °C 1.2: 1 h / 40 - 45 °C 2.1: sodium iodide / butanone / 16 h
	Multi-step reaction with 2 steps 1.1: iron(III) chloride / dichloromethane / 5 - 45 °C 1.2: 1.17 h / 40 - 45 °C 2.1: sodium iodide / butanone / 16 h
	Multi-step reaction with 3 steps 1: pyridine / dichloromethane / 5.5 h / 10 - 20 °C 2: iron(III) chloride / dichloromethane / 5 - 40 °C 3: potassium methylate / methanol / 2 h / 60 °C

	Multi-step reaction with 3 steps 1: pyridine / dichloromethane / 3.5 h / 10 - 20 °C 2: iron(III) chloride / dichloromethane / 5 - 40 °C 3: sodium hydroxide / methanol / 2 h / 65 °C
	Multi-step reaction with 3 steps 1: pyridine / dichloromethane / 6 h / 10 - 20 °C 2: aluminum (III) chloride / dichloromethane / 5 - 40 °C 3: hydrogenchloride; water / methanol / 3 h / 55 - 60 °C
	Multi-step reaction with 3 steps 1.1: iron(III) chloride / dichloromethane / 3.33 h / 5 - 20 °C 1.2: 0.83 h / 40 - 45 °C 2.1: sodium hydroxide / methanol / 3 h / Reflux 2.2: pH 6 3.1: pyridine / butan-1-ol / 14 h / 70 °C
	Multi-step reaction with 3 steps 1.1: iron(III) chloride / dichloromethane / 3.33 h / 5 - 20 °C 1.2: 0.83 h / 40 - 45 °C 2.1: sodium hydroxide / methanol / 3 h / Reflux 2.2: pH 6 3.1: pyridine / butan-1-ol / 14 h / 70 °C
	Multi-step reaction with 3 steps 1.1: iron(III) chloride / dichloromethane / 3.33 h / 5 - 20 °C 1.2: 0.83 h / 40 - 45 °C 2.1: sodium hydroxide / methanol / 3 h / Reflux 2.2: pH 6 3.1: sodium iodide; pyridine / butanone / 16.25 h / Reflux
	Multi-step reaction with 3 steps 1.1: iron(III) chloride / dichloromethane / 3.33 h / 5 - 20 °C 1.2: 0.83 h / 40 - 45 °C 2.1: sodium hydroxide; water / methanol / 3 h / pH 6 / Reflux 3.1: triacetoxyborohydride / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 3 steps 1.1: iron(III) chloride / dichloromethane / 3.33 h / 5 - 20 °C 1.2: 0.83 h / 40 - 45 °C 2.1: sodium hydroxide; water / methanol / 3 h / pH 6 / Reflux 3.1: sodium tetrahydroborate / 8 h / 55 °C
	Multi-step reaction with 3 steps 1.1: iron(III) chloride / dichloromethane / 3.33 h / 5 - 20 °C 1.2: 0.83 h / 40 - 45 °C 2.1: sodium hydroxide; water / methanol / 3 h / pH 6 / Reflux 3.1: sodium tetrahydroborate / 8 h / 55 °C 3.2: 0 °C
	Multi-step reaction with 3 steps 1.1: pyridine / dichloromethane / 0.5 h / 10 °C 1.2: 5.5 h / 10 °C 2.1: dichloromethane / 0.25 h / 5 °C 2.2: 0.5 h / 35 - 40 °C 3.1: hydrogenchloride / methanol / 3 h / 55 - 60 °C
	Multi-step reaction with 3 steps 1.1: pyridine / dichloromethane / 3.5 h / 10 - 20 °C 2.1: dichloromethane / 0.25 h / 5 °C 2.2: 1 h / 20 °C 3.1: sodium hydroxide / methanol / 2 h / 65 °C
	Multi-step reaction with 3 steps 1.1: pyridine / dichloromethane / 5.5 h / 10 - 20 °C 2.1: dichloromethane / 0.25 h / 5 °C 2.2: 1 h / 20 °C 3.1: sodium methylate / methanol / 2 h / 60 °C
	Multi-step reaction with 3 steps 1: N-chloro-succinimide / dichloromethane; acetonitrile / 2.33 h / -8 °C 2: magnesium / tetrahydrofuran / 2.67 h / 35 - 60 °C 3: iron(III) chloride / tetrahydrofuran / 1 h / 35 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: N-chloro-succinimide / dichloromethane; acetonitrile / 2.33 h / -8 °C 2: magnesium / tetrahydrofuran / 2.67 h / 35 - 60 °C 3: iron(III) chloride / tetrahydrofuran / 3 h / 35 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: N-Bromosuccinimide / dichloromethane; acetonitrile / 3.5 h / -8 °C 2: magnesium / tetrahydrofuran / 2.75 h / 32 - 62 °C 3: iron(III) chloride / tetrahydrofuran / 3 h / 35 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: iron(III) chloride / dichloromethane / 3.33 h / 5 - 20 °C 2: sodium hydroxide / methanol / 3 h / Reflux 3: triacetoxyborohydride / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 3 steps 1: iron(III) chloride / dichloromethane / 5 - 45 °C 2: sodium hydroxide / methanol / 3 h / Reflux 3: pyridine / butan-1-ol
	Multi-step reaction with 3 steps 1: iron(III) chloride / dichloromethane / 5 - 45 °C 2: sodium hydroxide / methanol / 3 h / Reflux 3: pyridine; sodium iodide / butanone / 16.25 h / Reflux

Reference： [1]Current Patent Assignee: SANOFI - WO2011/70380, 2011, A1
[2]Current Patent Assignee: SANOFI - WO2011/70380, 2011, A1
[3]Current Patent Assignee: SANOFI - WO2012/10913, 2012, A1
[4]Current Patent Assignee: SANOFI - WO2012/10913, 2012, A1
[5]Current Patent Assignee: SANOFI - WO2012/10913, 2012, A1
[6]Current Patent Assignee: SANOFI - WO2012/131409, 2012, A1
[7]Current Patent Assignee: SANOFI - WO2012/131409, 2012, A1
[8]Current Patent Assignee: SANOFI - WO2012/131409, 2012, A1
[9]Current Patent Assignee: SANOFI - WO2012/131410, 2012, A1
[10]Current Patent Assignee: SANOFI - WO2012/131410, 2012, A1
[11]Current Patent Assignee: SANOFI - WO2012/131410, 2012, A1
[12]Current Patent Assignee: SANOFI - US2013/131358, 2013, A1
[13]Current Patent Assignee: SANOFI - US2013/131358, 2013, A1
[14]Current Patent Assignee: SANOFI - US2013/131358, 2013, A1
[15]Current Patent Assignee: SANOFI - WO2013/178337, 2013, A1
[16]Current Patent Assignee: SANOFI - WO2013/178337, 2013, A1
[17]Current Patent Assignee: SANOFI - WO2013/178337, 2013, A1
[18]Current Patent Assignee: SANOFI - US2014/18554, 2014, A1
[19]Current Patent Assignee: SANOFI - US2014/114081, 2014, A1
[20]Current Patent Assignee: SANOFI - US2014/114081, 2014, A1

3
4-[3-(di-n-butylamino)-propoxy]-benzoic acid chloride hydrochloride [ No CAS ]
[ 437652-07-8 ]
[ 141626-36-0 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminum (III) chloride In dichloromethane at 0 - 10℃; for 20h;	14 Example 14 4-(3-Dibutylaminopropoxy)benzoyl chloride (71.8 g; 0.198 mol; 1.06 eq.) and N-(2-butylbenzofuran-5-yl)methanesulfonamide (50.0 g; 0.187 mol) were mixed in CH2Cl2 (350 mL) and cooled down to 0 °C. AlCl3 (99.7 g; 0.748 mol; 4.0 eq) was added, during addition (two hours) the temperature was kept between 0 - 5 °C. Reaction mixture was kept between 0 - 10 °C for twenty hours. Workup: Reaction mixture was poured on the mixture ice/HCl 1:1. Water was extracted once with 1000 mL and twice with 500 mL CH2Cl2. Organic layer was washed once with 1000 mL water and dried with Na2SO4. Solvent was evaporated on RVE. Product was transferred to the base: dissolved in CH2Cl2 and extracted with saturated solution of NaHCO3 and dried with Na2SO4. Yield was nearly quantitative as light brown foam. Confirmation: HR-MS, (M+H)+ = 557.3043

Reference： [1]Current Patent Assignee: TEVA PHARMACEUTICAL INDUSTRIES LTD. - EP2371808, 2011, A1 Location in patent: Page/Page column 11

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P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
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H412	Harmful to aquatic life with long-lasting effects
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 437652-07-8 ] {[proInfo.proName]}

Quality Control of [ 437652-07-8 ]

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Product Details of [ 437652-07-8 ]

Safety of [ 437652-07-8 ]

Application In Synthesis of [ 437652-07-8 ]

[ 437652-07-8 ] Synthesis Path-Downstream 1~3

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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