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256424-63-2

256424-63-2

Identification

  • Product Name:(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile

  • CAS Number: 256424-63-2

  • EINECS:

  • Molecular Weight:354.284

  • Molecular Formula: C14H9Cl2N3S2

  • HS Code:

  • Mol File:256424-63-2.mol

Synonyms:(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile

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Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:(S)-Luliconazole
  • Packaging:100mg
  • Price:$ 1325
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  • Manufacture/Brand:Crysdot
  • Product Description:(S,E)-2-(4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene)-2-(1H-imidazol-1-yl)acetonitrile 97%
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  • Manufacture/Brand:Alichem
  • Product Description:(S,E)-2-(4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene)-2-(1H-imidazol-1-yl)acetonitrile
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Relevant articles and documentsAll total 3 Articles be found

Imidazole acetonitrile derivative acid salt as well as preparation method and application thereof

-

Paragraph 0100; 0101, (2016/10/10)

The invention relates to an imidazole acetonitrile derivative acid salt as well as a preparation method and an application thereof, belongs to the technical field of drug synthesis, and aims to solve the problem about how to improve stability and increase the yield. The method comprises steps as follows: an imidazole acetonitrile derivative is dissolved in a water-insoluble polar organic solvent, then corresponding acid is added for a salt forming reaction, and the acid salt of the product imidazole acetonitrile derivative is gradually separated out, and applied to preparation of Luliconazole. The acid salt itself has better stability and used as an intermediate for preparing Luliconazole at the same time, the problem of mutual inversion of Z-E configuration in the Luliconazole preparation process can be solved, the Z configuration can be inverted into the E configuration, the configuration inversion stability is guaranteed, and the yield is higher. The effects of simple technology and easiness in operation are also realized.

Method for synthesizing Luliconazole

-

, (2016/10/09)

The invention relates to a method for synthesizing Luliconazole. The method comprises the steps of subjecting m-dichlorobenzene to Friedel-Crafts acylation with chloroacetyl chloride, catalytic chiral reduction with (S)-2-methyl-CBS-oxazaborolidine and esterification with methylsulfonyl chloride so as to obtain (S)-2,2',4'-ethyl trichlorobenzene methanesulfonate, and finally, subjecting (S)-2,2',4'-ethyl trichlorobenzene methanesulfonate to a reaction with carbon disulfide and imidazolyl acetonitrile, thereby obtaining Luliconazole. According to the method, the total yield is about 30%.

EXTERNAL PHARMACEUTICAL COMPOSITION

-

Page/Page column 7-8, (2009/01/24)

A pharmaceutical composition for external use, including: i) luliconazole represented by the following structural formula (1) and/or a salt thereof; and ii) one or two or more selected from N-methyl-2-pyrrolidone, propylene carbonate, and crotamiton.

Process route upstream and downstream products

Process route

(E)-(4S)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene(1H-imidazol-1-yl)acetonitrile hemifumarate

(E)-(4S)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene(1H-imidazol-1-yl)acetonitrile hemifumarate

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile
256424-63-2,187164-19-8

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile

Conditions
Conditions Yield
With water; sodium hydroxide; at 40 ℃; for 0.333333h;
92%
2-cyanomethyl-imidazole
23184-45-4

2-cyanomethyl-imidazole

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate
229334-55-8

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile
256424-63-2,187164-19-8

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile

Conditions
Conditions Yield
2-cyanomethyl-imidazole; With carbon disulfide; sodium hydroxide; In dimethyl sulfoxide; at 20 ℃; for 5h;
(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate; In dimethyl sulfoxide; at 20 ℃;
40%
luliconazole
187164-19-8

luliconazole

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile
256424-63-2,187164-19-8

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile

Conditions
Conditions Yield
With 1-methyl-pyrrolidin-2-one; In ethanol; at 40 - 60 ℃; for 336h; Reactivity;
With 1-methyl-pyrrolidin-2-one; lauric acid; hydrogenated castor oil; 1.3-butanediol; 1-Hexadecanol; glycerol; 2,6,10,15,19,23-hexamethyltetracosane; In water; at 40 ℃; for 336h; Reactivity;
With 1-methyl-pyrrolidin-2-one; 1,2-propylene cyclic carbonate; In ethanol; at 40 ℃; for 336h; Reactivity;
With 1-methyl-pyrrolidin-2-one; 1.3-butanediol; In ethanol; water; at 40 ℃; for 336h; Reactivity;
With 1,2-propylene cyclic carbonate; In ethanol; at 40 - 60 ℃; for 336h; Reactivity;
With N-ethyl-N-(2-methylphenyl)but-2-enamide; In ethanol; at 40 - 60 ℃; for 336h; Reactivity;
In ethanol; ethyl acetate; at 40 - 60 ℃; for 336h; Reactivity;
In ethanol; butanone; at 40 - 60 ℃; for 336h; Reactivity;
In ethanol; dimethyl sulfoxide; at 40 - 60 ℃; for 336h; Reactivity;
In ethanol; at 40 - 60 ℃; for 336h; Reactivity;
2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile
256424-63-2,187164-19-8

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane Ν,Ν-diethylaniline complex / toluene; tert-butyl methyl ether / 2.5 h / 0 °C
2.1: triethylamine / dichloromethane / 3 h / 10 °C
3.1: carbon disulfide; sodium hydroxide / dimethyl sulfoxide / 5 h / 20 °C
3.2: 20 °C
With carbon disulfide; borane Ν,Ν-diethylaniline complex; triethylamine; sodium hydroxide; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In dichloromethane; tert-butyl methyl ether; dimethyl sulfoxide; toluene;
1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile
256424-63-2,187164-19-8

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: aluminum (III) chloride / dichloromethane / 3 h / Reflux
2.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane Ν,Ν-diethylaniline complex / toluene; tert-butyl methyl ether / 2.5 h / 0 °C
3.1: triethylamine / dichloromethane / 3 h / 10 °C
4.1: carbon disulfide; sodium hydroxide / dimethyl sulfoxide / 5 h / 20 °C
4.2: 20 °C
With carbon disulfide; aluminum (III) chloride; borane Ν,Ν-diethylaniline complex; triethylamine; sodium hydroxide; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In dichloromethane; tert-butyl methyl ether; dimethyl sulfoxide; toluene;
(E)-(4S)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene(1H-imidazol-1-yl)acetonitrile hemifumarate

(E)-(4S)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene(1H-imidazol-1-yl)acetonitrile hemifumarate

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile
256424-63-2,187164-19-8

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile

Conditions
Conditions Yield
With water; sodium hydroxide; at 40 ℃; for 0.333333h;
92%
2-cyanomethyl-imidazole
23184-45-4

2-cyanomethyl-imidazole

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate
229334-55-8

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile
256424-63-2,187164-19-8

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile

Conditions
Conditions Yield
2-cyanomethyl-imidazole; With carbon disulfide; sodium hydroxide; In dimethyl sulfoxide; at 20 ℃; for 5h;
(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate; In dimethyl sulfoxide; at 20 ℃;
40%
luliconazole
187164-19-8

luliconazole

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile
256424-63-2,187164-19-8

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile

Conditions
Conditions Yield
With 1-methyl-pyrrolidin-2-one; In ethanol; at 40 - 60 ℃; for 336h; Reactivity;
With 1-methyl-pyrrolidin-2-one; lauric acid; hydrogenated castor oil; 1.3-butanediol; 1-Hexadecanol; glycerol; 2,6,10,15,19,23-hexamethyltetracosane; In water; at 40 ℃; for 336h; Reactivity;
With 1-methyl-pyrrolidin-2-one; 1,2-propylene cyclic carbonate; In ethanol; at 40 ℃; for 336h; Reactivity;
With 1-methyl-pyrrolidin-2-one; 1.3-butanediol; In ethanol; water; at 40 ℃; for 336h; Reactivity;
With 1,2-propylene cyclic carbonate; In ethanol; at 40 - 60 ℃; for 336h; Reactivity;
With N-ethyl-N-(2-methylphenyl)but-2-enamide; In ethanol; at 40 - 60 ℃; for 336h; Reactivity;
In ethanol; ethyl acetate; at 40 - 60 ℃; for 336h; Reactivity;
In ethanol; butanone; at 40 - 60 ℃; for 336h; Reactivity;
In ethanol; dimethyl sulfoxide; at 40 - 60 ℃; for 336h; Reactivity;
In ethanol; at 40 - 60 ℃; for 336h; Reactivity;
2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile
256424-63-2,187164-19-8

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane Ν,Ν-diethylaniline complex / toluene; tert-butyl methyl ether / 2.5 h / 0 °C
2.1: triethylamine / dichloromethane / 3 h / 10 °C
3.1: carbon disulfide; sodium hydroxide / dimethyl sulfoxide / 5 h / 20 °C
3.2: 20 °C
With carbon disulfide; borane Ν,Ν-diethylaniline complex; triethylamine; sodium hydroxide; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In dichloromethane; tert-butyl methyl ether; dimethyl sulfoxide; toluene;
1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile
256424-63-2,187164-19-8

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: aluminum (III) chloride / dichloromethane / 3 h / Reflux
2.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane Ν,Ν-diethylaniline complex / toluene; tert-butyl methyl ether / 2.5 h / 0 °C
3.1: triethylamine / dichloromethane / 3 h / 10 °C
4.1: carbon disulfide; sodium hydroxide / dimethyl sulfoxide / 5 h / 20 °C
4.2: 20 °C
With carbon disulfide; aluminum (III) chloride; borane Ν,Ν-diethylaniline complex; triethylamine; sodium hydroxide; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In dichloromethane; tert-butyl methyl ether; dimethyl sulfoxide; toluene;

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