Vu Tran

AM Lab
4/01/08

Experiment 46: Sulfa Drugs: Preparation of Sulfanilamide.

Aim: To prepare the sulfa drug sulfanilamide from acetamilide.

Reactions:

Apparatus:
Chemical Use:

Sodium Hydroxide 2.5 mL

Acetamilide 1.8 g
Chlorosulfoic Acid 5.0 mL
Ammonium Hydroxide 11 mL
Hydrochloric Acid 5.3 mL
Sodium Bicarbonate 5.0 g
Procedures:

1. Assemble apparatus as shown

2. Add 2.5 mL of 0.1 M Sodium hydroxide drop-wise to the glass wool
3. Place 1.8 g of acetamilide in a dry 50-mL Erlenmeyer flask
4. Melt the acetamilide by heating gently
5. Allow flask to cool to room temperature and cool in ice bath
6. In hood, transfer 5 mL of Chlorosulfonic acid to acetamilide in the flask
7. Attach the flask to the apparatus
8. Wait 10 mins, remove and heat additional 10 minutes in hot water bath at
70 C to complete the reaction. Cool in ice bath after
9. Add 30 g of crushed ice to 250 mL beaker
10. In hood, transfer the mixture with a pipet onto the ice while stirring the
mixture
11. Rinse the flask with 5 mL of cold water and transfer to beaker containing
the ice
12. Stir the precipitate to break up the lumps, filter with Buchner funnel
13. Finse the flask and beaker with 2x 5 mL ice water
14. Use the rinse water to wash the crude product on the funnel
15. In hood, prepare hot water bath at 70 C in 250 mL beaker
16. Place the crude into a 50 mL Erlenmeyer flask
17. Add 11 mL of dilute ammonium hydroxide. Stir to break up lump
18. Heat in hot water bath for 10 minutes.
19. Allow to cool, place in ice-water bath for several minutes
20. Collect the p-acetanidobezene sulfonamide on Buchner funnel
21. Rinse the flask and product with 10 mL ice water
22. Transfer solid to 25 mL round-bottom flask. Add 5.3 mL of dilute
Hydrochloric acid.
23. Add boiling stones. Attach reflux condenser. Heat till solid dissolve
24. Reflux for additional 5 minutes
25. Allow to cool to room temperature. If solid appears, boil again.
26. Transfer to 100 mL beaker. Add drop-wise 5.0 g of Sodium bicarbonate in
10 mL of water while stirring
27. Allow gas to cease before making the next addition
28. Sulfanolamide will begin to precipitate, begins to check for pH
29. pH range should be around 4-6
 30. Cool in ice-water bath. Collect on Buchner funnel
31. Rinse the beaker and solid with 5 mL of cold water
32. Weight the product and crystallize it from hot water
33. Allow the purified product to dry till next lab period
34. Weight the dry sulfanilamide and calculate % yield.
Caution:
1) Hot water, hot plate. Handle with care.
2) Chlorosulfonic acid is extreme noxious and corrosive chemical,
handle with care. Only dry glassware with this reagent. Be careful
when washing any glassware that has come in contact with it.

Data:
Crude before crystallization 1g
Sulfanilamide 0.48 g
Melting Point 164-167

Calculation:
Conclusion:

This experiment was good. However, we have a few accidents in part A of the lab.
Luckily none were hurt with major wounds. The rest of the experiment went smoothly.
We were successfully prepared the drug sulfanilamide from acetamilide. It was really
cool when the crystals started to crystallized at the end of the lab.

Questions & Answers:

1) Write an equation showing how excess chlorosulfonic acid is decomposed in

water.
A:

2) In the preparation of sulfanilamide, why was aqueous sodium bicarbonate, rather

than aqueous sodium hydroxide, used to neutralize the solution in the final step?.
A:

3) What is the structure of the polymer? Why does p-acetamidobenzenesulfonyl

chloride not produce?
A: