6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
With triphenylphosphine In tetrahydrofuran; tetrachloromethane for 3h; Reflux; | 97% |
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
With lithium chloride In N,N-dimethyl-formamide at 50℃; for 8h; | 95% |
6-chloro-5-(2-chloroacetyl) indolin-2-one
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
With triethylsilane; trifluoroacetic acid | |
Stage #1: 6-chloro-5-(2-chloroacetyl) indolin-2-one With triethylsilane; trifluoroacetic acid at 0 - 35℃; for 7h; Stage #2: With water at 5 - 10℃; for 1h; | |
With triethylsilane In trifluoroacetic acid at -5 - 45℃; for 7.5h; |
6-chloro-2-oxindole
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: AlCl3 / CS2 2: Et3SiH, CF3COOH View Scheme | |
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 1.2: 35 - 37 °C / Inert atmosphere 2.1: trifluoroacetic acid / 0.25 h / 25 - 30 °C / Inert atmosphere 2.2: 0 - 35 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 20 h / Reflux; Inert atmosphere 2: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / dichloromethane / 0 °C / Inert atmosphere View Scheme |
6-chloro-5-(2-chloroacetyl) indolin-2-one
A
6-chloro-5-(2-chloro-1-hydroxyethyl) indolin-2-one
B
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
With triethylsilane; trifluoroacetic acid for 7h; | |
With aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane In dichloromethane at 0℃; Inert atmosphere; chemoselective reaction; |
6-chloro-5-(2-chloro-1-hydroxyethyl) indolin-2-one
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
Stage #1: 6-chloro-5-(2-chloro-1-hydroxyethyl) indolin-2-one With trifluoroacetic acid at 20℃; for 1h; Stage #2: With triethylsilane at 35 - 40℃; for 13.5 - 15.5h; | |
Stage #1: 6-chloro-5-(2-chloro-1-hydroxyethyl) indolin-2-one With trifluoroacetic acid at 20℃; for 1h; Stage #2: With triethylsilane at 35 - 40℃; for 13.5 - 15.5h; |
2,5-dichloronitrobenzene
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: potassium carbonate / dimethyl sulfoxide / 25 - 30 °C / Inert atmosphere 1.2: 16 h / 40 - 85 °C 2.1: hydrogenchloride; tin / water; methanol / 10 - 70 °C 3.1: aluminum (III) chloride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 3.2: 35 - 37 °C / Inert atmosphere 4.1: trifluoroacetic acid / 0.25 h / 25 - 30 °C / Inert atmosphere 4.2: 0 - 35 °C / Inert atmosphere View Scheme |
dimethyl (4-chloro-2-nitrophenyl)malonate
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride; tin / water; methanol / 10 - 70 °C 2.1: aluminum (III) chloride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 2.2: 35 - 37 °C / Inert atmosphere 3.1: trifluoroacetic acid / 0.25 h / 25 - 30 °C / Inert atmosphere 3.2: 0 - 35 °C / Inert atmosphere View Scheme |
6-chloro-5-(2-chloroacetyl) indolin-2-one
A
6-chloro-5-(2-chloro-1-hydroxyethyl) indolin-2-one
C
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
With triethylsilane; aluminum (III) chloride In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere; Reflux; |
6-chloro-5-(2-chloroacetyl) indolin-2-one
B
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
With aluminum (III) chloride; dimethylmonochlorosilane In dichloromethane at 0℃; Inert atmosphere; chemoselective reaction; |
6-chloro-2-oxindole
A
6-chloro-5-(2-chloro-1-hydroxyethyl) indolin-2-one
C
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 20 h / Reflux; Inert atmosphere 2: aluminum (III) chloride; triethylsilane / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere; Reflux View Scheme |
6-chloro-2-oxindole
A
6-chloro-5-(2-chloro-1-hydroxyethyl) indolin-2-one
B
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 20 h / Reflux; Inert atmosphere 2: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / dichloromethane / 0 °C / Inert atmosphere View Scheme |
5-chloro-2,4-difluoronitrobenzene
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: N,N-dimethyl-formamide / 12 h / 100 °C 2: hydrogenchloride; acetic acid / water / 18 h / Reflux 3: thionyl chloride / 4 h / 20 °C 4: acetic acid; hydrogen / 3 h / 20 °C / 2327.23 Torr 5: sodium tetrahydroborate; lithium bromide; Trimethyl borate / tetrahydrofuran / 18 h / Reflux 6: triphenylphosphine / tetrahydrofuran; tetrachloromethane / 3 h / Reflux View Scheme | |
Multi-step reaction with 7 steps 1: N,N-dimethyl-formamide / 12 h / 100 °C 2: hydrogenchloride; acetic acid / water / 18 h / Reflux 3: thionyl chloride / 4 h / 20 °C 4: acetic acid; hydrogen / 3 h / 20 °C / 2327.23 Torr 5: sodium tetrahydroborate; lithium bromide; Trimethyl borate / tetrahydrofuran / 18 h / Reflux 6: triethylamine; dmap / dichloromethane / 5 h / Reflux 7: lithium chloride / N,N-dimethyl-formamide / 8 h / 50 °C View Scheme |
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: hydrogenchloride; acetic acid / water / 18 h / Reflux 2: thionyl chloride / 4 h / 20 °C 3: acetic acid; hydrogen / 3 h / 20 °C / 2327.23 Torr 4: sodium tetrahydroborate; lithium bromide; Trimethyl borate / tetrahydrofuran / 18 h / Reflux 5: triphenylphosphine / tetrahydrofuran; tetrachloromethane / 3 h / Reflux View Scheme | |
Multi-step reaction with 6 steps 1: hydrogenchloride; acetic acid / water / 18 h / Reflux 2: thionyl chloride / 4 h / 20 °C 3: acetic acid; hydrogen / 3 h / 20 °C / 2327.23 Torr 4: sodium tetrahydroborate; lithium bromide; Trimethyl borate / tetrahydrofuran / 18 h / Reflux 5: triethylamine; dmap / dichloromethane / 5 h / Reflux 6: lithium chloride / N,N-dimethyl-formamide / 8 h / 50 °C View Scheme |
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: thionyl chloride / 4 h / 20 °C 2: acetic acid; hydrogen / 3 h / 20 °C / 2327.23 Torr 3: sodium tetrahydroborate; lithium bromide; Trimethyl borate / tetrahydrofuran / 18 h / Reflux 4: triphenylphosphine / tetrahydrofuran; tetrachloromethane / 3 h / Reflux View Scheme | |
Multi-step reaction with 5 steps 1: thionyl chloride / 4 h / 20 °C 2: acetic acid; hydrogen / 3 h / 20 °C / 2327.23 Torr 3: sodium tetrahydroborate; lithium bromide; Trimethyl borate / tetrahydrofuran / 18 h / Reflux 4: triethylamine; dmap / dichloromethane / 5 h / Reflux 5: lithium chloride / N,N-dimethyl-formamide / 8 h / 50 °C View Scheme |
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetic acid; hydrogen / 3 h / 20 °C / 2327.23 Torr 2: sodium tetrahydroborate; lithium bromide; Trimethyl borate / tetrahydrofuran / 18 h / Reflux 3: triphenylphosphine / tetrahydrofuran; tetrachloromethane / 3 h / Reflux View Scheme | |
Multi-step reaction with 4 steps 1: acetic acid; hydrogen / 3 h / 20 °C / 2327.23 Torr 2: sodium tetrahydroborate; lithium bromide; Trimethyl borate / tetrahydrofuran / 18 h / Reflux 3: triethylamine; dmap / dichloromethane / 5 h / Reflux 4: lithium chloride / N,N-dimethyl-formamide / 8 h / 50 °C View Scheme |
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; lithium bromide; Trimethyl borate / tetrahydrofuran / 18 h / Reflux 2: triphenylphosphine / tetrahydrofuran; tetrachloromethane / 3 h / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; lithium bromide; Trimethyl borate / tetrahydrofuran / 18 h / Reflux 2: triethylamine; dmap / dichloromethane / 5 h / Reflux 3: lithium chloride / N,N-dimethyl-formamide / 8 h / 50 °C View Scheme |
2,4,5-Trichloronitrobenzene
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: potassium fluoride / N,N-dimethyl-formamide / 12 h / 125 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 12 h / 100 °C 3: hydrogenchloride; acetic acid / water / 18 h / Reflux 4: thionyl chloride / 4 h / 20 °C 5: acetic acid; hydrogen / 3 h / 20 °C / 2327.23 Torr 6: sodium tetrahydroborate; lithium bromide; Trimethyl borate / tetrahydrofuran / 18 h / Reflux 7: triphenylphosphine / tetrahydrofuran; tetrachloromethane / 3 h / Reflux View Scheme | |
Multi-step reaction with 8 steps 1: potassium fluoride / N,N-dimethyl-formamide / 12 h / 125 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 12 h / 100 °C 3: hydrogenchloride; acetic acid / water / 18 h / Reflux 4: thionyl chloride / 4 h / 20 °C 5: acetic acid; hydrogen / 3 h / 20 °C / 2327.23 Torr 6: sodium tetrahydroborate; lithium bromide; Trimethyl borate / tetrahydrofuran / 18 h / Reflux 7: triethylamine; dmap / dichloromethane / 5 h / Reflux 8: lithium chloride / N,N-dimethyl-formamide / 8 h / 50 °C View Scheme |
3-(1-piperazinyl)-1,2-benzisothiazole
6-chloro-5-(2-chloroethyl)-2-oxindole
ziprazidone
Conditions | Yield |
---|---|
With Morwet D425 In water Reflux; Inert atmosphere; | 92% |
In water Inert atmosphere; Reflux; dispersing agent; | 92% |
With potassium carbonate; potassium iodide In sulfolane at 75 - 100℃; for 2h; Product distribution / selectivity; | 75% |
6-chloro-5-(2-chloroethyl)-2-oxindole
ziprazidone
Conditions | Yield |
---|---|
With Morwet D425 In water Product distribution / selectivity; Reflux; Inert atmosphere; | 92% |
With sodium carbonate In water Product distribution / selectivity; Inert atmosphere; Reflux; Morwet D425; | 90% |
Stage #1: 3-(piperazin-1-yl)-1,2-benzisothiazole hydrochloride With potassium carbonate In acetonitrile for 0.5h; Stage #2: 6-chloro-5-(2-chloroethyl)-2-oxindole With sodium iodide In acetonitrile for 2h; Reflux; | 767 g |
6-chloro-5-(2-chloroethyl)-2-oxindole
7-bromo-3-piperazinyl-1,2-benzisothiazole
5-(2-(4-(7-bromo-1,2-benzisothiazol-3-yl)piperazinyl)-ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
With sodium carbonate In water at 115℃; for 20h; | 89% |
3-(1-piperazinyl)-1,2-benzisothiazole hydrochloride
6-chloro-5-(2-chloroethyl)-2-oxindole
ziprazidone
Conditions | Yield |
---|---|
With sodium carbonate In 1-methyl-pyrrolidin-2-one at 130 - 135℃; for 24h; Product distribution / selectivity; | 88.2% |
With sodium carbonate In poly(ethylene glycol) methyl ether at 120 - 125℃; for 48h; Product distribution / selectivity; | 88% |
With sodium carbonate; sodium iodide In toluene for 22.5h; Product distribution / selectivity; Heating / reflux; | 86% |
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In water at 105℃; for 12h; | 58% |
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetonitrile at 85℃; | 56% |
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
With sodium carbonate; sodium iodide In water for 24h; Reflux; | 51% |
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetonitrile at 80℃; | 8.7% |
3-(1-piperazinyl)-1,2-benzisothiazole
acetone
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
With potassium carbonate In water at 100℃; for 24h; Heating / reflux; | 3% |
6-chloro-5-(2-chloro-1-hydroxyethyl) indolin-2-one
3-(1-piperazinyl)-1,2-benzisothiazole
6-chloro-5-(2-chloroethyl)-2-oxindole
6-chloro-5-(2-chloroacetyl) indolin-2-one
A
5-(2-(4-(1,2-benzisothiazole-3-yl)-1-piperazinyl)-1-hydroxyethyl)-6-chloro-1,3-dihydro-2H-indole-2-one
B
5-(2-(4-(1,2-benzisothiazole-3-yl)-1-piperazinyl)-1-oxoethyl)-6-chloro-1,3-dihydro-2H-indole-2-one
C
ziprazidone
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; sodium carbonate; sodium iodide In cyclohexane Heating / reflux; |
6-chloro-5-(2-chloroethyl)-2-oxindole
ziprazidone
Conditions | Yield |
---|---|
With water; sodium carbonate; sodium iodide In N,N-dimethyl-formamide at 110℃; for 0.5h; Product distribution / selectivity; | |
With water; sodium carbonate; sodium iodide at 95 - 100℃; for 7.66667h; Product distribution / selectivity; |
3-(1-piperazinyl)-1,2-benzisothiazole
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
Stage #1: 3-(1-piperazinyl)-1,2-benzisothiazole; 6-chloro-5-(2-chloroethyl)-2-oxindole With sodium carbonate; sodium iodide In water; dimethyl sulfoxide at 115 - 125℃; for 2.75h; Stage #2: With hydrogenchloride In water for 0.166667h; |
1-(benzo[d]isoxazol-3-yl)piperazine hydrochloride
6-chloro-5-(2-chloroethyl)-2-oxindole
Conditions | Yield |
---|---|
Stage #1: 1-(benzo[d]isoxazol-3-yl)piperazine hydrochloride With sodium carbonate In water at 20℃; for 1h; Stage #2: 6-chloro-5-(2-chloroethyl)-2-oxindole With sodium iodide In water at 20 - 90℃; for 21 - 31h; Stage #3: In water at 45 - 80℃; for 1h; Product distribution / selectivity; |
Molecular Structure of 2H-Indol-2-one,6-chloro-5-(2-chloroethyl)-1,3-dihydro- (CAS NO.118289-55-7):
Empirical Formula: C10H9Cl2NO
Molecular Weight: 230.0906
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 2
Polar Surface Area: 29.1 Å2
Index of Refraction: 1.592
Molar Refractivity: 56.588 cm3
Molar Volume: 167.208 cm3
Surface Tension: 48.077 dyne/cm
Density: 1.376 g/cm3
Flash Point: 191.976 °C
Enthalpy of Vaporization: 64.376 kJ/mol
Boiling Point: 393.82 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C
Melting point: 218-221°C
Product Categories: Indole; Indoles; (intermediate of ziprasidone hcl); Intermediates of Ziprasidone
Hazard Codes: N
Risk Statements: 50/53
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 60-61
S60:This material and its container must be disposed of as hazardous waste.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
2H-Indol-2-one,6-chloro-5-(2-chloroethyl)-1,3-dihydro- , with CAS number of 118289-55-7, can be called 2H-indole-2-one,5-chloroethyl-6-chloro-1,3-dihydro ; 5-chloroethyl-6-chloro-1,3-dihydro-1h-indol-2-one ; 5-chloroethyl-6-chloro-1,3-dihydro-2h-indole-2-one ; 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2h-indol-2-one ; 5-(2-chloroethyl)-1,3-dihydro-2h-6-chloroindule-2-one ; 2h-indol-2-one-6-chloro-5-(2-chloroethyl)-1,3-dihydro ; 5-chloroethyl-6-chloro-1,3-dihydro-2h-indol-2-one ; 6-chloro-5-(2-chloroethyl)-1,3 .
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