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Synthesis of Sulfa Drug

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Carsen Popelka

on 17 July 2014

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Transcript of Synthesis of Sulfa Drug

Danielle Payne & Carsen Popelka
Step 1: Synthesis of Acetanilide
Run 1
Overview of Process
Step 2: Synthesis of
p-acetamidobenzenesulfonyl chloride
Synthesis of Sulfa Drug :
4-amino-N-benzylbenzene sulfonamide

Run 1
Overall Analysis of Synthesis
Step 3: Synthesis of acetylated sulfonamide
Step 4: Synthesis of pure sulfonamide
Run 1
Run 3
Run 1
Run 1
aniline
acetic anhydride
acetanilide
chlorosulfonic acid
p-acetamidobenzene sulfonyl chloride
4-amino-N-benzylbenzene sulfonamide
sodium bicarbonate
hydronium ion (acidic water)
acetylated sulfonamide
pyridine
acetonitrile
benzyl amine
Compounded error in volume due to multiple measurements

Small amount of undissolved oils (Run 1)

Crystal loss during filtration

Crystal loss due to spilling and transfer

Crystals may not have been fully dried when massed
Sources of Error
Lone pair on nitrogen attacks carbonyl carbon
Electrons from bond go to oxygen
Negatively charged oxygen plucks off hydrogen from amine
Analysis
Starting Amount :
1.700 mL Aniline

Theoretical Yield :
2.521 g Acetanilide

Actual Yield :
2.037 g Acetanilide

% Yield : 80.80%

Experimental Melting Point :
106.0 - 111.6 C

Literature Melting Point :
114.3 C

% Error in MP :
2.36 - 7.26 %

Analysis
Starting Amount :
2.150 mL Aniline

Theoretical Yield :
3.188 g Acetanilide

Actual Yield :
2.997 g Acetanilide

% Yield : 94.01 %

Experimental Melting Point :
110.2 - 112.6 C

Literature Melting Point :
114.3 C

% Error in MP :
1.49 - 3.59 %
Analysis
Starting Amount :
2.000 mL Aniline

Theoretical Yield :
2.966 g Acetanilide

Actual Yield :
2.699 g Acetanilide

% Yield : 90.99 %

Experimental Melting Point :
111.6 -113.5 C

Theoretical Melting Point :
114.3 C

% Error in MP :
0.70 - 2.36 %

Lone pair on oxygen of one chlorosulfonic acid attacks sulfur of another chlorosulfonic acid, chlorine leaves

Lone pair on chloride ion attacks positively charged sulfur

Lone pair on chlorine plucks off hydrogen of acetanilide

HCl leaves

Positive carbon attacks positive sulfur
Step 2 Mechanism Explained
Analysis
Starting Amount :
1.708 g Acetanilide

Theoretical Yield :
2.953 g
p-acetamidobenzenesulfonyl chloride

Actual Yield :
1.846 g
p-acetamidobenzenesulfonyl chloride

% Yield : 62.516 %

Experimental Melting Point :
125.8 - 126.0 C

Literature Melting Point :
146 C

% Error in MP :
13.70 - 13.84 %
Analysis
Step 3 Mechanism Explained
Analysis
Starting Amount :
2.533 g Acetanilide

Theoretical Yield :
4.385 g
p-acetamidobenzenesulfonyl
chloride

Actual Yield :
6.501 g
p-acetamidobenzenesulfonyl
chloride

% Yield : 148.25 %

Experimental Melting Point :
N/A

Literature Melting Point :
146 C

% Error in MP :
N/A
Starting Amount :
1.846 g
p-acetamidobenzenesulfonyl
chloride

Theoretical Yield :
2.401 g
N-[4-(benzylsfulamoyl) phenyl]
acetamide

Actual Yield :
1.321 g
N-[4-(benzylsulfamoyl) phenyl]
acetamide

% Yield : 55.02 %

Experimental Melting Point :
195.1 - 197.4 C

Literature Melting Point :
215.21 C

% Error in MP :
8.28 - 9.34 %
Starting Amount :
1.212 g aminated sulfonamide

Theoretical Yield :
1.045 g 4-amino-N-benzylbenzene
sulfonamide

Actual Yield :
0.939 g 4-amino-N-benzylbenzene
sulfonamide

% Yield : 89.86 %

Experimental Melting Point :
176.2 - 178.9 C

Literature Melting Point :
172.12 C

% Error in MP :
2.37 - 3.94 %

IR Spectrum
HNMR Spectrum
Run 2
Run 2
Analysis
Starting Amount :
2.793 g Acetanilide

Theoretical Yield :
4.829 g
p-acetamidobenzenesulfonyl
chloride

Actual Yield :
2.587 g
p-acetamidobenzenesulfonyl
chloride

% Yield : 53.576 %

Experimental Melting Point :
> 195 C

Literature Melting Point :
146 C

% Error in MP :
> 33.6 %
Run 2
Analysis
Starting amount :
2.324 g
p-aceamidobenzenesulfonyl
chloride

Theoretical Yield :
3.023 g
N-[4-(benzylsulfamoyl) phenyl]
acetamide

Actual Yield :
0 g
N-[4-(benzylsulfamoyl) phenyl]
acetamide

% Yield : 0 %
Analysis
Sources of Error
Analysis
Aniline stored overnight - product loss due to transfer

Residual error due to undissolved oils in production of aniline (Run 1)

Chance that miniscule amount of acetanilide failed to dissolve in chlorosulfonic acid

Chance that not all of product was isolated in filtration

Product loss due to filtration

Chance of some polymerization while drying under frys lamp (Run 1, Run 2)

Crystals in Run 3 not dried under frys lamp before mass was measured

No melting point taken (Run 3)

No IR taken (Run 2, Run 3)

No HNMR taken (Run 2, Run 3)
Lone pair on nitrogen of benzyl amine attacks sulfur, forcing pi electrons onto oxygen
Lone pair on negatively charged oxygen clamps down, forcing chlorine to leave
Addition of hydride ion plucks off hydrogen from positively charged nitrogen of amine, leaving end product
Sources of Error
Run 3
Sources of Error
Starting amount :
6.501 g
p-acetamidobenzenesulfonyl chloride

Theoretical Yield :
10.258 g
N-{4-[(4-bromophenyl)sulfamoyl] phenyl} acetamide

Actual Yield :
0 g
N-{4-[(4-bromophenyl) sulfamoyl] phenyl} acetamide

% Yield : 0 %
Run 3
Step 4 Mechanism Explained
Lone pair on carbonyl oxygen attacks hydrogen ion (from HCl)

Resonance exhibited

Lone pair on oxygen of water molecule attacks carbonyl carbon, forming a hydrate

Heat dehydrates molecule, reforming the carbonyl group

Lone pair on oxygen clamps down, forcing the amine to leave

Nitrogen attacks a hydrogen ion from solution, giving itself a positive charge

Reaction with sodium bicarbonate deprotonates the nitrogen and produces carbon dioxide, water, and sodium ion
Crystals continued to form in filtrate after filtration complete - due to time restraints, crystals not isolated (Run 1)

Compounded error from polymerization in drying of Step 2 product (Run 2)

Solutions not originally supersaturated - no crystals produced

All three samples sat in EtOH for at least 2 days

EtOH had to be evaporated off and added again to induce crystal formation

Sample 3 bumped while evaporating EtOH off - no crystals rescued
Starting Volume :
1.700 mL aniline

Theoretical Yield :
4.892 g
4-amino-N-benzylbenzene
sulfonamide

Actual Yield :
0.939 g
4-amino-N-benzylbenzene
sulfonamide

% Yield : 19.19 %
Compounded error from all previous steps

Possibility that not all crystals were dissolved

Possibility that not all crystals reacted
Full transcript