Isobutyl iodide → N-(tert-Butyl)-5-isobutylthiophene-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]CCCC.I[CH2:20][CH:21]([CH3:23])[CH3:22]>C1COCC1>[CH2:20]([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)[CH:21]([CH3:23])[CH3:22]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
N-tert-Butylthiophene-2-sulfonamide (10 g, 0.046 mol, see step (a) above) was dissolved in THF (85 mL) under N2 and then cooled to −78° C. n-BuLi (1.6 M, 76.9 mL, 0.12 mol) was added via a syringe. The reaction mixture was stirred at −78° C. for 30 min. and then at −40° C. for 2 h. Iodo-2-methylpropane (10.5 mL, 0.09 mol) was added dropwise to the reaction mixture. The reaction mixture was stirred overnight at room temperature. The reaction was quenched with NH4Cl (aq.) and extracted with EtOAc. The combined organic phase was washed with brine and dried and concentrated in vacuo. The crude product was purified on column chromatography (hexanes:EtOAc (10:1)) to give the sub-title compound in 55% yield (7.0 g, 0.025 mol).
Workup
- additionwas added via a syringe
- waitat −40° C. for 2 h
- stirringThe reaction mixture was stirred overnight at room temperature
- customThe reaction was quenched with NH4Cl (aq.)
- extractionextracted with EtOAc
- washThe combined organic phase was washed with brine
- customdried
- concentrationconcentrated in vacuo
- customThe crude product was purified on column chromatography (hexanes:EtOAc (10:1))
Sources & evidence
- ORD record
- ord-07238348ced540b3bebb4b74d34f5ea7
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08080571B2
Reaction notes
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