Toluene → N-(Tert-butyl)-2-thiophenesulfonamide

HRID 562547Notes

Reaction equation

HRID 562547 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6](Cl)(=[O:8])=[O:7].[C:10]([NH2:14])([CH3:13])([CH3:12])[CH3:11].C1(C)C=CC=CC=1>C(Cl)(Cl)Cl>[C:10]([NH:14][S:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:8])=[O:7])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6385Tert-ButylamineHCID 855182-Thiophenesulfonyl chloride

Product 1

HCID 765814N-(Tert-butyl)-2-thiophenesulfonamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Thiophene-2-sulfonyl chloride (15 g, 0.082 mol) was dissolved in CHCl3 (200 mL) under N2 atmosphere and then cooled to 0° C. tert-Butylamine (25.9 mL, 0.246 mol) dissolved in CHCl3 (50 mL) was then added dropwise to the reaction mixture. The reaction mixture was stirred for 1 h at room temperature and then at reflux for 10 min. Toluene (700 mL) was added and the organic phase was washed with water (3×50 mL), dried, and concentrated in vacuo. The sub-title product was used without further purification in the next step.

Workup

  1. additionwas then added dropwise to the reaction mixture
  2. temperatureat reflux for 10 min
  3. washthe organic phase was washed with water (3×50 mL)
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe sub-title product was used without further purification in the next step

Sources & evidence

ORD record
ord-c397e25afdd04dc3a9ccd93cbdf8f02f
Source dataset
uspto-grants-2011_11
Patent number
US08067418B2

Reaction notes

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