Hydrochloric Acid → N-(1,1-Dimethylethyl)-2-formyl-1-methyl-1H-pyrrole-3-sulfonamide

HRID 820

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].CN(C)[CH:17]=[O:18].Cl>C1COCC1>[CH3:4][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[CH:17]=[O:18])(=[O:8])=[O:7])([CH3:1])[CH3:3]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 12.96 g (60 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 300 mL THF under a nitrogen atmosphere cooled to -78° C. was added dropwise, at such a rate as to keep the temperature below -65° C., 52.35 mL (123 mmol) 2.35M n-butylithium in hexanes. The reaction was stirred at -78° C. for ca. 30 minutes. To the reaction mixture was added 4.64 mL (60 mmol) of N,N-dimethylformamide dropwise. The reaction mixture was allowed to warm to room temperature and stir for ca. 2 hours. The reaction mixture was cooled to 0° C. and acidified with 1N HCl. The THF phase was separated, washed with brine, dried (MgSO4) and concentrated in vacuo. The crude residue was chromatographed on silica (25% ethyl acetate/80% hexanes) affording 5.72 g of the title compound as a white solid, m.p. 101.5°-103° C.

Workup

additionwas added dropwise
temperatureto warm to room temperature
stirringstir for ca. 2 hours
temperatureThe reaction mixture was cooled to 0° C.
customThe THF phase was separated
washwashed with brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe crude residue was chromatographed on silica (25% ethyl acetate/80% hexanes)

Sources & evidence

ORD record: ord-1689ec83ac2b4e2e9bc10359a96a617b
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723410

Linked notes

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