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Chemical Structure| 120511-88-8 Chemical Structure| 120511-88-8

Structure of 120511-88-8

Chemical Structure| 120511-88-8

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Product Details of [ 120511-88-8 ]

CAS No. :120511-88-8
Formula : C15H18N2O
M.W : 242.32
SMILES Code : CC(C)(C1=CC(CO)=CC(C(C)(C#N)C)=C1)C#N
MDL No. :MFCD16619241

Safety of [ 120511-88-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 120511-88-8 ]

* 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 [ 120511-88-8 ]

[ 120511-88-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 120511-88-8 ]
  • [ 13578-51-3 ]
  • [ 120511-73-1 ]
YieldReaction ConditionsOperation in experiment
Synthesis of Anastrozole Mesylate To a stirred solution of 2 g (8.25 mmol) of 2-[3-(cyano-dimethyl-methyl)-5-hydroxymethyl-phenyl]-2-methyl-propionitrile in 20 ml of dry tetrahydrofuran 0.248 g (8.25 mmol) of sodium hydride as 80% suspension in mineral oil was added. The mixture was heated to 70 C. for 30 minutes. The mixture was then evaporated on rotary evaporator and solid residue was suspended in 10 mL of dimethylacetamide and 1.84 g (8.25 mmol) of <strong>[13578-51-3]1-(p-toluenesulfonyl)-1,2,4-triazole</strong> was added portion-wise. The mixture was stirred 20 minutes at ambient temperature (the reaction is slightly exothermic). Dimethylacetamide was evaporated under vacuum to leave viscous oily residue. The residue was partitioned between dichloromethane (20 mL) and water (20 mL). The layers were separated and dichloromethane layer was washed with water (20 mL). Aqueous layers were combined and washed with dichloromethane (20 mL). Combined dichloromethane layers were dried over Na2SO4, the drying agent was filtered off and filtrate was evaporated to give 2.58 g of oil. The oil was dissolved in ethylacetate (20 mL) and such amount of methane sulfonic acid was gradually added until liquid phase was acidic (indicator paper). Precipitated anastrozole mesylate was separated by filtration; it was washed with ethylacetate (2×5 mL) and dried at 50 C. to give 2.53 g of product (78% of theoretical yield).
Synthesis of Anastrozole Mesylate To stirred solution of 2 g (8.25 mmol) of 2-[3-(cyano-dimethyl-methyl)-5-hydroxymethyl-phenyl]-2-methyl-propionitrile in 20 ml of dry dioxane 0.248 g (8.25 mmol) of sodium hydride as 80% suspension in mineral oil was added. The mixture was heated to 70 C. for 30 minutes. To the solution of alcoholate cooled to 10 C. 1.84 g (8.25 mmol) of <strong>[13578-51-3]1-(p-toluenesulfonyl)-1,2,4-triazole</strong> was added portion wise. The mixture was stirred 20 minutes at ambient temperature, and then it was heated to 80 to 100 C. for 3 hours. The mixture was evaporated in vacuo, the remainder was partitioned between 30 ml dichloromethane and 30 ml of water. The organic extract was dried over magnesium sulfate. After filtering off the drying agent and evaporation in vacuo 2.5 g of crude anastrozole in the form of a light orange oil was obtained. The residue was dissolved in ethylacetate (20 mL) and such amount of methane sulfonic acid was gradually added until liquid phase was acidic (indicator paper). Precipitated anastrozole mesylate was separated by filtration; it was washed with ethylacetate (2×5 mL) and dried at 50 C. to give 2.09 g of product (65% of theoretical yield); Example 6 Synthesis of Anastrozole Mesylate To stirred solution of 21.71 g (89.59 mmol) of 2-[3-(cyano-dimethyl-methyl)-5-hydroxymethyl-phenyl]-2-methyl-propionitrile in 200 ml of dry dioxane 2.69 g (89.59 mmol) of sodium hydride as 80% suspension in mineral oil was added. The mixture was heated in oil bath (batch temperature) 75-85 C. for 35 minutes. The mixture was cooled down and additional amount of dioxane (100 ml) was added. To this mixture 20.00 g (89.59 mmol) of <strong>[13578-51-3]1-(p-toluenesulfonyl)-1,2,4-triazole</strong> was added followed by additional amount of dioxane (50 ml). The mixture was gradually heated (bath temperature 115 to 125 C.) and stirred at this temperature range for total 5 hours. The mixture was then cooled down and it was left overnight. The mixture was evaporated using rotary evaporator and oily residue was partitioned between 300 ml of dichloromethane and 300 ml of water. The organic extract was dried over magnesium sulfate. After filtering off the drying agent and evaporation in vacuo 26.2 g of crude anastrozole in the form of oil was obtained. The residue was dissolved in ethylacetate (200 mL) and such amount of methanesulfonic acid was gradually added until liquid phase was acidic (indicator paper, total amount of methanesulfonic acid was 7.2 g). Precipitated anastrozole mesylate was separated by filtration; it was washed with ethylacetate (2×50 mL) and dried at 50 C. to give 24.0 g of product (68.7% of theoretical yield).
Synthesis of Anastrozole Mesylate To stirred solution of 2 g (8.25 mmol) of 2-[3-(cyano-dimethyl-methyl)-5-hydroxymethyl-phenyl]-2-methyl-propionitrile in 20 ml of dry dimethoxyethane 0.248 g (8.25 mmol) of sodium hydride as 80% suspension in mineral oil was added. The mixture was heated to 70 C. for 30 minutes. To the solution of alcoholate cooled to 10 C. 1.84 g (8.25 mmol) of <strong>[13578-51-3]1-(p-toluenesulfonyl)-1,2,4-triazole</strong> was added portion wise. The mixture was stirred 20 minutes at ambient temperature, and then it was heated to 80 to 100 C. for 3 hours. The mixture was evaporated in vacuo, the remainder was partitioned between 30 ml dichloromethane and 30 ml of water. The organic extract was dried over magnesium sulfate. After filtering off the drying agent and evaporation in vacuo 2.58 g of crude anastrozole in the form of a light orange oil was obtained. The residue was dissolved in ethylacetate (20 mL) and such amount of methane sulfonic acid was gradually added until liquid phase was acidic (indicator paper). Precipitated anastrozole mesylate was separated by filtration; it was washed with ethylacetate (2×5 mL) and dried at 50 C. to give 1.02 g of product (32% of theoretical yield).
Synthesis of Anastrozole Mesylate To stirred solution of 2 g (8.25 mmol) of 2-[3-(cyano-dimethyl-methyl)-5-hydroxymethyl-phenyl]-2-methyl-propionitrile in 20 ml of dry tetrahydrofuran 0.248 g (8.25 mmol) of sodium hydride as 80% suspension in mineral oil was added. The mixture was heated to 70 C. for 30 minutes. To the solution of alcoholate cooled to 10 C. 1.84 g (8.25 mmol) of <strong>[13578-51-3]1-(p-toluenesulfonyl)-1,2,4-triazole</strong> was added portion-wise. The mixture was stirred 20 minutes at ambient temperature, and then it was heated to 80 to 100 C. for 3 hours. The mixture was evaporated in vacuo, the remainder was partitioned between 20 ml dichloromethane and 20 ml of water. The organic extract was dried over magnesium sulfate. After filtering off the drying agent and evaporation in vacuo 2.6 g of crude anastrozole in the form of yellow oil was obtained. The residue was dissolved in ethylacetate (20 mL) and such amount of methane sulfonic acid was gradually added until liquid phase was acidic (indicator paper). Precipitated anastrozole mesylate was separated by filtration; it was washed with ethylacetate (2×5 mL) and dried at 50 C. to give 1.79 g of product (55% of theoretical yield).

 

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