Butyl iodide → 5-Butyl-N-tert-butylthiophene-2-sulfonamide

HRID 1644831Notes

Reaction equation

HRID 1644831 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].ICCCC>C1COCC1>[C:1]([NH:5][S:6]([C:9]1[S:10][C:11]([CH2:15][CH2:16][CH2:17][CH3:18])=[CH:12][CH:13]=1)(=[O:7])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 765814N-(Tert-butyl)-2-thiophenesulfonamideHCID 178418339Butyllithium

Product 1

HCID 119939045-Butyl-N-tert-butylthiophene-2-sulfonamideYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

N-tert-Butylthiophene-2-sulfonamide (5 g, 0.0228 mol, see Example 1(a) above) was dissolved in THF (43 mL) under N2 and then cooled to −78° C. n-BuLi (1.6 M, 38.5 mL, 0.062 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-butane (5.19 mL, 0.046 mol) was added dropwise to the reaction mixture. The reaction mixture was stirred overnight at room temperature, quenched with NH4Cl (aq) and extracted with EtOAc. The combined organic phase was washed with brine, dried and concentrated in vacuo. The crude product was purified on column chromatography (Hex:EtOAc 10:1) to give the sub-title compound in 46% yield (2.92 g, 0.011 mol).

Workup

  1. additionwas added via a syringe
  2. waitat −40° C. for 2 h
  3. stirringThe reaction mixture was stirred overnight at room temperature
  4. customquenched with NH4Cl (aq)
  5. extractionextracted with EtOAc
  6. washThe combined organic phase was washed with brine
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified on column chromatography (Hex:EtOAc 10:1)

Sources & evidence

ORD record
ord-787d4bf4a90f45b09e1771374fe77f66
Source dataset
uspto-grants-2012_02
Patent number
US08124638B2

Reaction notes

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