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6th February 2013 @ 03:12

Pyrrole Sulfonamide formation was attempted in deuterated chloroform to make it easier to investigate using 1H NMR.



Reaction start time:  11:00 AM EST 5/2/13
MD 6-5 (20 mg, 0.068 mmol, 1 equiv.) was stirred in deuterated chloroform (2 mL) 1H NMR spectrum was taken. Thionyl chloride (20 µL, 0.068 mmol, 1 equiv.) was added, 1H NMR taken. The reaction was then stirred at room temperature overnight, a solution was made with N-methyl benzylamine (12 µL) and pyridine (5 mL). In the morning thionyl chloride was removed under reduced atmosphere leaving a brownish black residue. 340 µL of the N-methyl benzylamine:pyridine solution was added to the residue and after an hour pyridine was removed under reduced pressure and a 1H NMR spectrum was taken.

NMR data:

NMREXP_1.pdf
:
MD 6-5 doesn't dissolve in d-chloroform.

NMREXP_2.pdf
: After addition of thionyl chloride MD 6-5 seems to dissolve in d-chloroform but NMR not conclusive.

NMREXP_3.pdf
:
After 20 hours thionyl chloride is removed and spectrum indicates what seems to be MD 6-5 (perhaps chlorinated or maybe just not a salt anymore) in d-chloroform.

NMREXP_4.pdf
:
After addition of N-methyl benzylamine and pyridine followed by removal of pyridine. Spectrum shows residiual pyridine and very little N-methyl benzylamine (added too little of the amine it seems).

N-methylbenzylamine.pdf
: Spectrum of N-methyl benzylamine in d-chloroform.

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

Risk and Hazard assessment:
Same as Synthesis of N-benzyl-1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonamide (MD 12-2)
Attached Files
NMREXP_4.pdf
NMREXP_3.pdf
NMREXP_2.pdf
NMREXP_1.pdf
N-methylbenzylamine.pdf
N-methylbenzylamine.pdf