Provide details about the reation workup. How is this product purified , and what methods were used to prove they had the right material ?   N-ETHYLALLENIMINE[Aziridine, 1-ethyl-2-methylene-] Submitted by Albert T. Bottini and Robert E. Olsen1.Checked by Thomas H. Lowry and E. J. Corey. 1. ProcedureCaution! This preparation should be carried out in a good hood to avoid exposure to ammonia. The operator should wear rubber gloves and protective goggles because 2-haloallylamines and ethylenimines can cause severe skin and eye irritation.A 2-l. three-necked flask is fitted with a sealed mechanical stirrer, a gas-inlet tube, and a dry ice condenser protected from the air by a soda-lime drying tube (Note 1). The system is flushed thoroughly with dry ammonia, and 32.8 g. (0.84 mole) of sodium amide (Note 2) is added to the flask. The system is again flushed with ammonia, the condenser is provided with dry ice covered by acetone, and 1.2 l. of liquid ammonia is condensed in the flask. The gas-inlet tube is replaced with a dropping funnel, the stirrer is started, and 118 g. (0.72 mole) of N-(2-bromoallyl)ethylamine2 is added dropwise in 20–30 minutes; during the addition, the ammonia boils vigorously, and the color of the slurry changes from gray to black. Stirring is continued for 3 hours, and the dry ice is then allowed to evaporate. The condenser is provided with an ice-salt mixture, and the ammonia is allowed to evaporate until the volume is reduced to about 800 ml. (Note 3). Ethanol-free ether (200 ml.) is added rapidly through the dropping funnel, and the reaction is stopped by the slow, dropwise addition (Caution!) of 5 ml. of water. The ammonia is allowed to evaporate overnight. Water (150 ml.) and 100 ml. of ether are added to the residue, and the mixture is stirred for 2 minutes in order to dissolve the precipitated salts. The resulting mixture, which consists of aqueous and ethereal solutions, is separated, and the aqueous phase is extracted with 75 ml. of ether. The ether solutions are combined, dried over sodium hydroxide (Note 4), and distilled through an efficient low-holdup column (Note 5). The fraction with b.p. 77–80°, n25D 1.4260–1.4268, which is 96–97% N-ethylallenimine (Note 6), weighs 30–34 g. (48–55%). Pure (>99.5%) N-ethylallenimine has b.p. 77–79°, n25D 1.4281–1.4284 (Note 7) and (Note 8).

Curren'S Math For Meds: Dosages & Sol
11th Edition
ISBN:9781305143531
Author:CURREN
Publisher:CURREN
Chapter10: Reconstitution Of Powdered Drugs
Section: Chapter Questions
Problem 7.2P
icon
Related questions
icon
Concept explainers
Question

Provide details about the reation workup.

How is this product purified , and what methods were used to prove they had the right material ?

 

N-ETHYLALLENIMINE
[Aziridine, 1-ethyl-2-methylene-]

Submitted by Albert T. Bottini and Robert E. Olsen1.
Checked by Thomas H. Lowry and E. J. Corey.


1. Procedure
Caution! This preparation should be carried out in a good hood to avoid exposure to ammonia. The operator should wear rubber gloves and protective goggles because 2-haloallylamines and ethylenimines can cause severe skin and eye irritation.
A 2-l. three-necked flask is fitted with a sealed mechanical stirrer, a gas-inlet tube, and a dry ice condenser protected from the air by a soda-lime drying tube (Note 1). The system is flushed thoroughly with dry ammonia, and 32.8 g. (0.84 mole) of sodium amide (Note 2) is added to the flask. The system is again flushed with ammonia, the condenser is provided with dry ice covered by acetone, and 1.2 l. of liquid ammonia is condensed in the flask. The gas-inlet tube is replaced with a dropping funnel, the stirrer is started, and 118 g. (0.72 mole) of N-(2-bromoallyl)ethylamine2 is added dropwise in 20–30 minutes; during the addition, the ammonia boils vigorously, and the color of the slurry changes from gray to black. Stirring is continued for 3 hours, and the dry ice is then allowed to evaporate. The condenser is provided with an ice-salt mixture, and the ammonia is allowed to evaporate until the volume is reduced to about 800 ml. (Note 3). Ethanol-free ether (200 ml.) is added rapidly through the dropping funnel, and the reaction is stopped by the slow, dropwise addition (Caution!) of 5 ml. of water. The ammonia is allowed to evaporate overnight. Water (150 ml.) and 100 ml. of ether are added to the residue, and the mixture is stirred for 2 minutes in order to dissolve the precipitated salts. The resulting mixture, which consists of aqueous and ethereal solutions, is separated, and the aqueous phase is extracted with 75 ml. of ether. The ether solutions are combined, dried over sodium hydroxide (Note 4), and distilled through an efficient low-holdup column (Note 5). The fraction with b.p. 77–80°, n25D 1.4260–1.4268, which is 96–97% N-ethylallenimine (Note 6), weighs 30–34 g. (48–55%). Pure (>99.5%) N-ethylallenimine has b.p. 77–79°, n25D 1.4281–1.4284 (Note 7) and (Note 8).

AI-Generated Solution
AI-generated content may present inaccurate or offensive content that does not represent bartleby’s views.
steps

Unlock instant AI solutions

Tap the button
to generate a solution

Knowledge Booster
Macromolecules
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, biology and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Curren'S Math For Meds: Dosages & Sol
Curren'S Math For Meds: Dosages & Sol
Nursing
ISBN:
9781305143531
Author:
CURREN
Publisher:
Cengage
Basic Clinical Laboratory Techniques 6E
Basic Clinical Laboratory Techniques 6E
Biology
ISBN:
9781133893943
Author:
ESTRIDGE
Publisher:
Cengage