Hydrochloric Acid → 3-[[(1,1-dimethylethyl)amino]sulfonyl]N,N,1-trimethyl-1H-pyrrole-2-carboxamide

HRID 1081244

Reaction equation

HRID 1081244 reaction equation
[CH3:1][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].C([Li])CCC.[CH3:20][N:21]([CH3:25])[C:22](Cl)=[O:23].[Cl-].[NH4+].Cl>C1COCC1>[CH3:4][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[C:22]([N:21]([CH3:25])[CH3:20])=[O:23])(=[O:8])=[O:7])([CH3:1])[CH3:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6598Dimethylcarbamoyl ChlorideHCID 25517Ammonium ChlorideHCID 19693811N-(1,1-Dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamideHCID 178418339Butyllithium

Product 1

HCID 196938293-[[(1,1-dimethylethyl)amino]sulfonyl]N,N,1-trimethyl-1H-pyrrole-2-carboxamideYield 50.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 6.48 g (30 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 150 mL, THF under a nitrogen atmosphere cooled to -78° C. was added dropwise, at such a rate as to keep the temperature below -60° C., 25 mL (61.5 mmol) 2.46M n-butyllithium in hexanes. The reaction mixture was stirred at -78° C. for ca. 30 minutes. To the reaction mixture was added dropwise a solution of 3.1 mL (33 mmol) of N,N-dimethylcarbamyl chloride in 10 mL of THF at such a rate as to maintain the temperature below -65° C. The reaction mixture was allowed to warm to room temperature and stir for ca. 1.5 hours. The reaction mixture was cooled to ca. 5° C. and 60 mL of 50% ammonium chloride solution was added. The reaction mixture was stirred for ca. 15 minutes. The pH was adjusted to ca. 3 with 1N HCl (ca. 30 mL), and the aqueous phase was separated from the THF phase and extracted with ethyl acetate. The combined THF and ethyl acetate extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to an oil. The oil was chromatographed on silica with (20% ethyl acetate/80% n-butyl chloride) affording 4.33 g of the title compound as a pale yellow solid.

Workup

  1. additionwas added dropwise
  2. temperatureto maintain the temperature below -65° C
  3. temperatureto warm to room temperature
  4. stirringstir for ca. 1.5 hours
  5. temperatureThe reaction mixture was cooled to ca. 5° C.
  6. stirringThe reaction mixture was stirred for ca. 15 minutes
  7. customthe aqueous phase was separated from the THF phase
  8. extractionextracted with ethyl acetate
  9. washThe combined THF and ethyl acetate extracts were washed with brine
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated in vacuo to an oil
  12. customThe oil was chromatographed on silica with (20% ethyl acetate/80% n-butyl chloride)

Sources & evidence

ORD record
ord-18e289bdfdb744b49e3a6e88f3be3e0f
Source dataset
uspto-grants-1996_12
Patent number
US05585328

Linked notes

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