2-n-butyl-5-bromo-benzofuran
methanesulfonamide
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
With bis(dibenzylideneacetone)-palladium(0); tert-butyl XPhos In 1,4-dioxane at 100℃; for 24h; Reagent/catalyst; Solvent; Inert atmosphere; | 100% |
5-amino 2-n-butyl benzofuran
methanesulfonyl chloride
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
With ammonia In tetrahydrofuran; tert-butyl methyl ether; water at 200℃; |
2-(4-bromo-2-formylphenoxy)-hexanoic acid
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: benzenesulfonyl chloride; triethylamine / toluene; water / 80 °C 2: tert-butyl XPhos; bis(dibenzylideneacetone)-palladium(0) / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere View Scheme |
5-bromosalicyclaldehyde
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 80 °C 2: sodium hydroxide; water / 20 - 40 °C 3: benzenesulfonyl chloride; triethylamine / toluene; water / 80 °C 4: tert-butyl XPhos; bis(dibenzylideneacetone)-palladium(0) / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere View Scheme |
Ethyl 2-bromohexanoate
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 80 °C 2: sodium hydroxide; water / 20 - 40 °C 3: benzenesulfonyl chloride; triethylamine / toluene; water / 80 °C 4: tert-butyl XPhos; bis(dibenzylideneacetone)-palladium(0) / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere View Scheme |
ethyl 2-(4-bromo-2-formylphenoxy)-hexanoate
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide; water / 20 - 40 °C 2: benzenesulfonyl chloride; triethylamine / toluene; water / 80 °C 3: tert-butyl XPhos; bis(dibenzylideneacetone)-palladium(0) / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere View Scheme |
2-bromohexanoic acid
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: thionyl chloride / 5 h / Reflux 2.1: aluminum (III) chloride / dichloromethane / Cooling with ice 2.2: 20 °C 3.1: sodium hydroxide / methanol / 4 h / 65 °C 4.1: sodium tetrahydroborate / 2 h 5.1: hydrogenchloride / water / 6 h / Reflux 6.1: tetrabutyl-ammonium chloride / tetrahydrofuran / 4 h / 60 °C / Reflux View Scheme |
2-bromohexanoyl chloride
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: aluminum (III) chloride / dichloromethane / Cooling with ice 1.2: 20 °C 2.1: sodium hydroxide / methanol / 4 h / 65 °C 3.1: sodium tetrahydroborate / 2 h 4.1: hydrogenchloride / water / 6 h / Reflux 5.1: tetrabutyl-ammonium chloride / tetrahydrofuran / 4 h / 60 °C / Reflux View Scheme |
4-methoxy-aniline
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: chloroform / 2 h / Inert atmosphere 2.1: aluminum (III) chloride / dichloromethane / Cooling with ice 2.2: 20 °C 3.1: sodium hydroxide / methanol / 4 h / 65 °C 4.1: sodium tetrahydroborate / 2 h 5.1: hydrogenchloride / water / 6 h / Reflux 6.1: tetrabutyl-ammonium chloride / tetrahydrofuran / 4 h / 60 °C / Reflux View Scheme |
4-methoxyacetanilide
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: aluminum (III) chloride / dichloromethane / Cooling with ice 1.2: 20 °C 2.1: sodium hydroxide / methanol / 4 h / 65 °C 3.1: sodium tetrahydroborate / 2 h 4.1: hydrogenchloride / water / 6 h / Reflux 5.1: tetrabutyl-ammonium chloride / tetrahydrofuran / 4 h / 60 °C / Reflux View Scheme |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sodium hydroxide / methanol / 4 h / 65 °C 2: sodium tetrahydroborate / 2 h 3: hydrogenchloride / water / 6 h / Reflux 4: tetrabutyl-ammonium chloride / tetrahydrofuran / 4 h / 60 °C / Reflux View Scheme |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / 2 h 2: hydrogenchloride / water / 6 h / Reflux 3: tetrabutyl-ammonium chloride / tetrahydrofuran / 4 h / 60 °C / Reflux View Scheme |
2-n-butyl-5-aminobenzofuran hydrochloride
methanesulfonyl chloride
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride In tetrahydrofuran at 60℃; for 4h; Reflux; |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
benzoyl chloride
N-benzoyl-N'-(2-n-butyl-1-benzofuran-5-yl)-methanesulfonamide
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 10 - 20℃; for 6h; | 100% |
Stage #1: N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide With pyridine In dichloromethane at 10℃; for 0.5h; Stage #2: benzoyl chloride In dichloromethane at 10℃; for 5.5h; |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
With sodium hydroxide In water at 5 - 70℃; Product distribution / selectivity; | 95% |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
With potassium hydroxide In water at 5 - 20℃; for 3h; Product distribution / selectivity; | 94% |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
Stage #1: N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide With potassium hydroxide In water for 0.5h; Stage #2: With magnesium chloride In water at 5 - 25℃; Product distribution / selectivity; | 93.7% |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
Stage #1: N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide With potassium hydroxide In water for 0.5h; Stage #2: With calcium chloride In water at 5 - 25℃; Product distribution / selectivity; | 92% |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
With iron(III) chloride In dichloromethane for 2h; Heating / reflux; | 90% |
aluminum (III) chloride In dichloromethane at 25℃; for 2h; | 90% |
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 |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
propionyl chloride
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 10 - 20℃; for 3.5h; | 84% |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
With N-chloro-succinimide In dichloromethane; acetonitrile at -8℃; for 2.33333h; | 76% |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
With lithium hydroxide In water at 0 - 20℃; for 9h; | 74.5% |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
4-[(3-carbethoxyamino)-propoxy]benzoylchloride
N-[2-butyl-3-{4-[(3-ethoxycarbonylamino)propoxy]benzoyl}-1-benzofuran-5-yl]-methanesulfonamide
Conditions | Yield |
---|---|
With iron(III) chloride In dichloromethane at 5 - 45℃; | 72.1% |
Stage #1: N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide; 4-[(3-carbethoxyamino)-propoxy]benzoylchloride With iron(III) chloride In dichloromethane at 5 - 20℃; for 3.33333h; Stage #2: With water In dichloromethane at 40 - 45℃; for 0.833333h; | |
Stage #1: N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide; 4-[(3-carbethoxyamino)-propoxy]benzoylchloride With iron(III) chloride In dichloromethane at 5 - 20℃; for 3.33333h; Stage #2: With water In dichloromethane at 40 - 45℃; for 0.833333h; | |
With iron(III) chloride In dichloromethane at 5 - 20℃; for 3.33333h; |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
With N-Bromosuccinimide In dichloromethane; acetonitrile at -8℃; for 3.5h; | 71% |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
4-<3-(dibutylamino)propoxy>benzaldehyde
N-(2-butyl-3-((4-(3-(dibutylamino)propoxy)phenyl)(hydroxy)methyl)benzofuran-5-yl)methanesulfonamide
Conditions | Yield |
---|---|
Stage #1: N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide With n-butyllithium In hexane at 20℃; for 2h; Stage #2: 4-<3-(dibutylamino)propoxy>benzaldehyde In tetrahydrofuran; hexane at 20℃; for 2h; Reagent/catalyst; Solvent; Temperature; Time; Concentration; | 40% |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
4-(3-chloropropoxy)benzoic acid chloride
N-(2-butyl-3-(4-(3-chloropropoxy)benzoyl)benzofuran-5-yl)methanesulfonamide
Conditions | Yield |
---|---|
Stage #1: N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide; 4-(3-chloropropoxy)benzoic acid chloride; iron(III) chloride In dichloromethane at 5 - 45℃; Stage #2: With water In dichloromethane at 40 - 45℃; for 1h; Product distribution / selectivity; |
4-(3-bromopropoxy)benzoyl chloride
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
C23H26BrNO5S
Conditions | Yield |
---|---|
Stage #1: 4-(3-bromopropoxy)benzoyl chloride; N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide; iron(III) chloride In dichloromethane at 5 - 45℃; Stage #2: With water In dichloromethane at 40 - 45℃; for 1.16667h; Product distribution / selectivity; |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
dronedarone
Conditions | Yield |
---|---|
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 View Scheme | |
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 View Scheme | |
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 View Scheme |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: iron(III) chloride / dichloromethane / 5 - 45 °C 1.2: 1 h / 40 - 45 °C 2.1: sodium iodide / butanone / 16 h 3.1: hydrogenchloride / isopropyl alcohol; water / 5 h / 0 °C View Scheme | |
Multi-step reaction with 3 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 3.1: hydrogenchloride / isopropyl alcohol; water / 5 h / 0 °C View Scheme |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
dronedarone
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 0 - 10℃; for 20h; |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
acetyl chloride
N-acetyl-N'-(2-n-butyl-1-benzofuran-5-yl)-methanesulfonamide
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 10 - 20℃; for 5.5h; | |
With pyridine In dichloromethane at 10 - 20℃; for 5.5h; |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
N-[2-n-butyl-3-[4-[3-(di-n-butylamino)propoxy]benzoyl]-1-benzofuran-5-yl]-N'-benzoyl-methanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 6 h / 10 - 20 °C 2: aluminum (III) chloride / dichloromethane / 5 - 40 °C View Scheme |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
N-[2-n-butyl-3-[4-[3 (-di-n-butylamino)propoxy]benzoyl]-1-benzofuran-5-yl]-N'-acetyl-methanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 5.5 h / 10 - 20 °C 2: iron(III) chloride / dichloromethane / 5 - 40 °C View Scheme | |
Multi-step reaction with 2 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 View Scheme |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 3.5 h / 10 - 20 °C 2: iron(III) chloride / dichloromethane / 5 - 40 °C View Scheme |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
N-[2-butyl-3-{4-[(3-amino)propoxy]benzoyl}-1-benzofuran-5-yl]-methansulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 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 View Scheme | |
Multi-step reaction with 2 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 View Scheme | |
Multi-step reaction with 2 steps 1: iron(III) chloride / dichloromethane / 3.33 h / 5 - 20 °C 2: sodium hydroxide / methanol / 3 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: iron(III) chloride / dichloromethane / 5 - 45 °C 2: sodium hydroxide / methanol / 3 h / Reflux View Scheme |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
N-[2-n-butyl-3-[4-[3 (-di-n-butylamino)propoxy]benzoyl]-1-benzofuran-5-yl]-N'-ethoxycarbonyl-methanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 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 View Scheme |
N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 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 View Scheme |
The CAS register number of 2-Butyl-5-[methanesulfonamido]benzofuran is 437652-07-8. It also can be called as Methanesulfonamide, N-(2-butyl-5-benzofuranyl)- and the systematic name about this chemical is N-(2-butyl-1-benzofuran-5-yl)methanesulfonamide. The molecular formula about this chemical is C13H17NO3S and the molecular weight is 267.34. It belongs to the API.
Physical properties about 2-Butyl-5-[methanesulfonamido]benzofuran are: (1)ACD/LogP: 3.97; (2)ACD/LogD (pH 5.5): 3; (3)ACD/LogD (pH 7.4): 3; (4)ACD/BCF (pH 5.5): 249; (5)ACD/BCF (pH 7.4): 248; (6)ACD/KOC (pH 5.5): 1807; (7)ACD/KOC (pH 7.4): 1800; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 67.69Å2; (12)Index of Refraction: 1.596; (13)Molar Refractivity: 72.405 cm3; (14)Molar Volume: 212.663 cm3; (15)Polarizability: 28.704x10-24cm3; (16)Surface Tension: 49.235 dyne/cm; (17)Enthalpy of Vaporization: 65.064 kJ/mol; (18)Boiling Point: 399.861 °C at 760 mmHg.
You can still convert the following datas into molecular structure:
(1)SMILES: O=S(=O)(Nc2cc1c(oc(c1)CCCC)cc2)C
(2)InChI: InChI=1/C13H17NO3S/c1-3-4-5-12-9-10-8-11(14-18(2,15)16)6-7-13(10)17-12/h6-9,14H,3-5H2,1-2H3
(3)InChIKey: HACDESLXZXBASP-UHFFFAOYAP
(4)Std. InChI: InChI=1S/C13H17NO3S/c1-3-4-5-12-9-10-8-11(14-18(2,15)16)6-7-13(10)17-12/h6-9,14H,3-5H2,1-2H3
(5)Std. InChIKey: HACDESLXZXBASP-UHFFFAOYSA-N
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