Grad Dip Arylpyrrole

 

N.B Benzylamine was used instead of N-methylbenzylamine so the experiment numbering was changed from MD 10-2 to MD 12-1.

Synthesis of N-benzyl-1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonamide via sulfonyl chloride.



Reaction start time: 11:30 AM EST 31/10/12
MD 6-3 (95 mg, 0.34 mmol, 1 equiv.) was stirred in Acetonitrile (10 mL). Thionyl chloride (25 µL, 0.34 mmol, 1 equiv.) and the brown mixture went dark brown after 1 minute. At 12:30 PM DMF (100 µL, 1 mmol) was added.

At 5:00 PM the mixture was concentrated under reduced atmosphere leaving behind a dark brown residue.

See also:

Risk and Hazard assessment:
Same as MD 10-1: Synthesis of N-benzyl-1-(4-fluorophenyl)-N,2,5-trimethyl-1H-pyrrole-3-sulfonamide (MD 10-1) except with starting material doubled and solvent changed from DCM to acetonitrile.

Synthesis of N3,N4-dibenzyl-1-(4-fluorophenyl)-N3,N4,2,5-tetramethyl-1H-pyrrole-3,4-disulfonamide via sulfonyl chloride.



Reaction start time: 10:05 AM EST 26/10/12

See also:
Chlorination and sulfonamide formation method

Risk and Hazard assessment:

Synthesis of 1-amino-2-methyl-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate using copper perchlorate tetrabenzyl cyclam.



Reaction start time: 1:30 PM EST 25/10/12

See also:
Synthesis of 1-amino-2-methyl-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate MD (5-1)
Upscaled synthesis of 1-amino-2-methyl-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate MD (5-2)

Risk and Hazard assessment:
Same as Synthesis of 1-amino-2-methyl-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate MD (5-1) except silver oxide is replaced with copper perchlorate tetrabenzyl cyclam (Cu cyclam).
Hazard statement for Cu cyclam: Unknown assume toxic

Synthesis of 1-amino-2-methyl-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate in the presence of TEMPO to explore if the reaction occurs via a radical intermediate.



Reaction start time: EST 25/10/12

See also:
Synthesis of 1-amino-2-methyl-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (MD 5-3)
Upscaled synthesis of 1-amino-2-methyl-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate MD (5-2)
Synthesis of 1-amino-2-methyl-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate MD (5-1)

Risk and Hazard assessment:
Same as Synthesis of 1-amino-2-methyl-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate MD (5-1) except with addition of 2,2,6,6-Tetramethyl-1-piperidinyloxy (TEMPO).
Hazard statements for TEMPO: Causes severe skin burns and eye damage.

Synthesis of 1-amino-2-methyl-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate using Copper Iodide instead of Silver Oxide.



Reaction start time: EST 25/10/12

See also:
Upscaled synthesis of 1-amino-2-methyl-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate MD (5-2)
Synthesis of 1-amino-2-methyl-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate MD (5-1)

Risk and Hazard assessment:
Same as Synthesis of 1-amino-2-methyl-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate MD (5-1) except replacement of Silver oxide (Ag₂O) with Copper Iodide (CuI).
Hazard statements for CuI: Harmful if swallowed, causes skin irritation, causes serious eye irritation, may cause respiratory irritation, very toxic to aquatic life with long lasting effects.