Methyl iodide → N-(1,1-Dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide

HRID 812

Reaction equation

HRID 812 reaction equation
[CH3:1][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][NH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].CI.[CH3:16]C(C)([O-])C.[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:4][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:16])[CH:10]=1)(=[O:8])=[O:7])([CH3:1])[CH3:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 19693846N-(tert-Butyl)-1H-pyrrole-3-sulfonamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 19693811N-(1,1-Dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of N-(1,1-dimethylethyl)-1H-pyrrole-3 -sulfonamide 9 g (0.044 mol) in 90 mL N,N-dimethylforamide was cooled to 15° C. under a nitrogen atmosphere. To this was added 3.2 mL (0.053 mol) of methyl iodide followed by 5.43 g (0.048 mol) of potassium t-butoxide. The mixture was warmed at ca. 60° C. for 2 hours then allowed to cool to room temperature and stirred for ca. 2 hours. The reaction mixture was diluted with ethyl acetate, washed three times with 1N HCl, once with brine, dried (MgSO4) and evaporated to an oily solid which was triturated with 5% diethyl ether/95% hexanes affording 6 g of the title compound as a beige solid, m.p. 134°-135° C.

Workup

  1. temperatureto cool to room temperature
  2. washwashed three times with 1N HCl
  3. dry with materialonce with brine, dried (MgSO4)
  4. customevaporated to an oily solid which
  5. customwas triturated with 5% diethyl ether/95% hexanes affording 6 g of the title compound as a beige solid, m.p. 134°-135° C.

Sources & evidence

ORD record
ord-c014829738084401b0a152f2e7cdf4bb
Source dataset
uspto-grants-1998_03
Patent number
US05723410

Linked notes

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