Tert-Butylamine → 5-Bromo-N-tert-butylthiophene-2-sulfonamide

HRID 1484876Notes

Reaction equation

HRID 1484876 reaction equation
[Br:1][C:2]1[S:6][C:5]([S:7](Cl)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[C:11]([NH2:15])([CH3:14])([CH3:13])[CH3:12]>O1CCOCC1>[Br:1][C:2]1[S:6][C:5]([S:7]([NH:15][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:9])=[O:8])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 27339245-Bromothiophene-2-sulfonyl chloride

Product 1

HCID 27571875-Bromo-N-tert-butylthiophene-2-sulfonamideYield 94.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 5-bromothiophene-2-sulfonyl chloride (1.5 g, 5.74 mmol, 1.0 equiv.), t-BuNH2 (1.26 g, 17.22 mmol, 3.0 equiv.) in 1,4-dioxane (50 ml) was stirred at 20° C. for 4 h under nitrogen atmosphere. The reaction mixture was concentrated to give a residue, which was purified by silica gel chromatography (PE/EA 100:1 to 10:1 as eluent) to afford 5-bromo-N-tert-butylthiophene-2-sulfonamide (1.614 g, 94.3%) as solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give a residue, which
  3. customwas purified by silica gel chromatography (PE/EA 100:1 to 10:1 as eluent)

Sources & evidence

ORD record
ord-609d968bab1148caa5c10b3108a2e4e2
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

Loading…