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Organic Chemistry II Synthesis

Results of our semester long lab synthesizing a sulfa- drug.
by

Ian Quinn

on 5 December 2012

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Transcript of Organic Chemistry II Synthesis

Recovered product from step 3 was placed into a flask and 10 mL of 6M HCl was added,
Mixture was stirred and heated until boiling, which was continued until complete dissolution.
The solution was cooled to room temperature and saturated sodium bicarbonate was added until the pH was neutralized.
Cool in ice and vacuum filter.
Recrystallize using ethanol.
Dry under the fries lamp. Step 1: Acetylation of Aniline 2 ml of Aniline was added to an Erlynmyer with 15 mL of distilled water.
2.62 uL of Acetic Anhydride was added to the flask, followed by 37.3 mL of distilled water.
Heat and stirring were applied until all solid was dissolved.
Product was filtered and allowed to dry.
2.753 g of product were measured post-drying. By: Ashleigh Stewart & Ian Quinn Organic Chemistry II Synthesis Results The dry acetanilide was placed into a flask while 6.06 ml chlorosulfonic acid was slowly added.
The flask was placed into a warm water bath to complete the dissolution.
After the oil was cooled, portions were slowly pipetted off and placed in a beaker to remain on ice.
The product was then vacuum filtered and washed with cold water, and placed under the fries lamp to dry.
The final product was placed in the desiccator. Step 2: Synthesis of p-Acetamidobenzenesulfonyl Chloride Step 3: Synthesis of Acetylated Sulfonamide Step two product, p-acetamidobenzenesulfonyl chloride was placed into a flask.
19.69 g of acetonitrile were added.
2.166 g of p-bromoaniline were placed into 8.66 ml of pyridine to be dissolved.
This solution was the added to the flask and stirred at room temperature for several minutes.
After checking the reaction progress using the TLC, the reaction was acidified using 6M HCl. The ethyl acetate was then extracted.
The organic layer was washed with
1. Water
2. Saturated NaCl
And then dried with MgSO4
The dry organic layer was then concentrated and recrystallized using an ethanol/water mixture. Step 3 Continued: Results: Our first attempt failed due to the use of ice in our product during step two. The ice is not filtered and contains ions that interacted with our final product. With this correction our second time through was much better and received better yields. This lab was good at enforcing lab techniques and teaching us to think for ourselves to accomplish a goal. Discussion: Step 4: Removal of Acetyl Group, Purification of 4-amino-N-(4-bromophenyl)benzenesulfonamide
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