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molecular formula C15H17ClN2 B193210 Anastrozole EP Impurity I CAS No. 120511-91-3

Anastrozole EP Impurity I

Cat. No. B193210
M. Wt: 260.76 g/mol
InChI Key: HSNGPKBBTHINTG-UHFFFAOYSA-N
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Patent
USRE036617

Procedure details

A solution of 2,2'-(5-chloromethyl-1,3-phenylene)di(2-methylpropiononitrile), (0.23 g), and 1H-1,2,4-triazole (0.35 g) in acetonitrile (2 ml) was heated under reflux for 18 h, then evaporated to dryness. The residue was partitioned between 1N aqueous potassium hydrogen carbonate solution and ethyl acetate, the organic phase was separated, dried and evaporated to dryness under reduced pressure, and the residue was purified by flash column chromatography. Elution with methanol:chloroform (1:49 by volume), gave 2,2'-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]di(2-methylpropiononitrile), identical with the product of Example 1, and further elution with methanol:chloroform (2:23 by volume, gave 2,2'-[5-(4H-1,2,4-triazol-4-ylmethyl)-1,3-phenylene]di(2-methylpropiononit rile), mp. 158°-161°.
Quantity
0.23 g
Type
reactant
Reaction Step One
Quantity
0.35 g
Type
reactant
Reaction Step One
Quantity
2 mL
Type
solvent
Reaction Step One

Identifiers

REACTION_CXSMILES
Cl[CH2:2][C:3]1[CH:4]=[C:5]([C:14]([CH3:18])([CH3:17])[C:15]#[N:16])[CH:6]=[C:7]([C:9]([CH3:13])([CH3:12])[C:10]#[N:11])[CH:8]=1.[NH:19]1[CH:23]=[N:22][CH:21]=[N:20]1>C(#N)C>[N:19]1([CH2:2][C:3]2[CH:4]=[C:5]([C:14]([CH3:18])([CH3:17])[C:15]#[N:16])[CH:6]=[C:7]([C:9]([CH3:13])([CH3:12])[C:10]#[N:11])[CH:8]=2)[CH:23]=[N:22][CH:21]=[N:20]1

Inputs

Step One
Name
Quantity
0.23 g
Type
reactant
Smiles
ClCC=1C=C(C=C(C1)C(C#N)(C)C)C(C#N)(C)C
Name
Quantity
0.35 g
Type
reactant
Smiles
N1N=CN=C1
Name
Quantity
2 mL
Type
solvent
Smiles
C(C)#N

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
under reflux for 18 h
Duration
18 h
CUSTOM
Type
CUSTOM
Details
evaporated to dryness
CUSTOM
Type
CUSTOM
Details
The residue was partitioned between 1N aqueous potassium hydrogen carbonate solution and ethyl acetate
CUSTOM
Type
CUSTOM
Details
the organic phase was separated
CUSTOM
Type
CUSTOM
Details
dried
CUSTOM
Type
CUSTOM
Details
evaporated to dryness under reduced pressure
CUSTOM
Type
CUSTOM
Details
the residue was purified by flash column chromatography
WASH
Type
WASH
Details
Elution with methanol:chloroform (1:49 by volume)

Outcomes

Product
Name
Type
product
Smiles
N1(N=CN=C1)CC=1C=C(C=C(C1)C(C#N)(C)C)C(C#N)(C)C

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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