All Notebooks | Help | Support | About
Archives
Authors
Sections
Tools
Show/Hide Keys
26th February 2013 @ 05:51

Synthesis of 2-(1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonamido)acetamide with longer time spent stirring with amine.

 

 

Reaction start time: 12:30 PM EST 25/2/13
MD 6-5 (150 mg, 0.51 mmol, 1 equiv) and Phosphorous Pentachloride (105 mg, 0.68 mmol, 1 equiv) were mixed at room temperature in dry diethyl ether (10 mL) for 2 hours under an inert atmosphere. After 2 hours the mixture was filtered and to the filtrate was added pyridine (260 µL, 2.0 mmol, 3.9 equiv.) followed by 2-aminoacetamide (100 mg, 1.3 mmol, 2.5 equiv.). Reaction was left stirring for 3 hours at room temperature. Reaction was concentrated under reduced pressure leaving a brown residue (14 mg).

Linked Posts
Attached Files
21st February 2013 @ 03:30

Synthesis of 2-(1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonamido)acetamide for testing as an anti-malarial.

 

 

Reaction start time: 1:00 PM EST 20/2/13
MD 6-5 (200 mg, 0.68 mmol, 1 equiv) and Phosphorous Pentachloride (144 mg, 0.68 mmol, 1 equiv) were mixed at room temperature in dry diethyl ether (10 mL) for 2 hours under an inert atmosphere. After 2 hours the mixture was filtered and to the filtrate was added pyridine (260 µL, 2.0 mmol, 2.9 equiv.) followed by 2-aminoacetamide (100 mg, 1.3 mmol, 1.9 equiv.) Reaction was concentrated under reduced pressure leaving a brown residue  (21 mg).

See also:
Chlorination of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate (MD 15-1), Synthesis of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate (MD 6-5)

 NMR Data: 

MD_26-1_crude.pdf
: Crude residue.

MD_26-1_fraction_1-2.pdf
: Clean fraction that looks to be a sulfonamide

Risk and hazard assessment:

MD 25-1 RA.pdf
Attached Files
18th February 2013 @ 05:56

Chlorination of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate using Phosphorous pentachloride.



Reaction start time: 5:00 PM EST 18/2/13
MD 6-5 (100 mg, 0.34 mmol, 1 equiv) and Phosphorous Pentachloride (72 mg, 0.34 mmol, 1 equiv) were mixed at room temperature in dry diethyl ether (5 mL) for 2 hours under an inert atmosphere. After 2 hours the mixture was filtered and to the filtrate was added pyridine (44 µL, 0.68 mmol, 2 equiv.) followed by N-methylbenzylamine (70 µL, 0.68 mmol, 2 equiv.), after addition a cloudy yellow percipitate formed. Removal of solvent under reduced atmosphere left behind a thick yellow oil (36 mg).

See also:
Chlorination of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate (MD 15-1), Synthesis of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate (MD 6-5)

Risk and Hazard assessment: Same asChlorination of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate (MD 15-1)

18th February 2013 @ 05:01

Investigation of sulfonamide synthesis by via NMR.

 

Reaction time: 4:00 PM EST, 15/2/13

Three reactions were set up: A, B and C. To each reaction was added MD 6-5 (30 mg, 0.10 mmol, 1 equiv.) dissolved in d-DMSO (1 mL) followed by cooling in an ice bath. Thionyl chloride (60 µL, 0.20 mmol, 2 equiv.) was then added to each one. was left stirring for 1 minute before quenching, was left stirring for 5 minutes before quenching and C was left stirring for 30 minutes before quenching. The reactions were quenched with a solution of pyridine (22 µL, 0.20 mmol, 2 equiv.) and N-methylbenzylamine (35 µL, 0.20 mmol, 2 equiv.). NMRs of each were then taken.

 

See also: Synthesis of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate (MD 6-5)

Synthesis of N-benzyl-1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonamide (MD 12-5)


Risk and hazard assessment: Same as Synthesis of N-benzyl-1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonamide (MD 12-2)

18th February 2013 @ 04:04

NMR investigation of the chlorination of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate using Phosphorous pentachloride.



Reaction start time: 10:15 AM EST 14/2/12
MD 6-5 (50 mg, 0.17 mmol, 1 equiv) and Phosphorous Pentachloride (36 mg, 0.17 mmol, 1 equiv) were mixed at room temperature in d-DMSO (2 mL) for 2 hours after which a H1 NMR spectrum was taken.

NMR data:

PCl5NMR_1.pdf
:


See also:
Chlorination of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate (MD 15-1), Synthesis of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate (MD 6-5)

Risk and Hazard assessment: Same as Chlorination of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate (MD 15-1)Chlorination of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate (MD 15-1)
Attached Files