Butyl iodide → 5-Butyl-N-tert-butylthiophene-2-sulfonamide
Reaction equation
[C:1]([NH:5][S:6]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li][CH2:15][CH2:16][CH2:17][CH3:18].C(I)CCC>C1COCC1>[CH2:15]([C:11]1[S:10][C:9]([S:6]([NH:5][C:1]([CH3:4])([CH3:2])[CH3:3])(=[O:7])=[O:8])=[CH:13][CH:12]=1)[CH2:16][CH2:17][CH3:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 2-(N-t-butylaminosulfonyl)thiophene (2.01 g, 9.18 mmol) in anhydrous THF (17 mL) cooled to -78° C. under N2 was added 2.5 M n-BuLi (10 mL, 2.7 equiv). After stirring at -78° C. for 30 min the bath temperature was raised to -40° C. and the mixture was stirred for an additional 2 hrs. To this mixure was added n-butyliodide (2.0 mL, 2 equiv) and the reaction was allowed to warm to room temperature. After stirring overnight the darkened reaction mixture was quenched with NH4Cl soln and extracted with EtOAc. The organic was washed with brine and dried over anhydrous MgSO4 and concentrated in vacuo. The titled compound was purified by flash chromatography eluting with hex/EtOAc (15:1 to 7:1). Rf=0.32 (6:1 Hex/EtOAc).
Workup
- temperaturewas raised to -40° C.
- stirringthe mixture was stirred for an additional 2 hrs
- temperatureto warm to room temperature
- stirringAfter stirring overnight the darkened reaction mixture
- customwas quenched with NH4Cl soln
- extractionextracted with EtOAc
- washThe organic was washed with brine
- dry with materialdried over anhydrous MgSO4
- concentrationconcentrated in vacuo
- customThe titled compound was purified by flash chromatography
- washeluting with hex/EtOAc (15:1 to 7:1)
Sources & evidence
- ORD record
- ord-8389f400a1af47a6b5ad28bade2099fa
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05444067
Reaction notes
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