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

HRID 465411Notes

Reaction equation

HRID 465411 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[S:11](Cl)(=[O:13])=[O:12]>O1CCCC1>[CH3:2][C:1]([NH:5][S:11]([C:7]1[S:6][CH:10]=[CH:9][CH:8]=1)(=[O:13])=[O:12])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 855182-Thiophenesulfonyl chloride

Product 1

HCID 765814N-(Tert-butyl)-2-thiophenesulfonamideYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of t-butylamine (8.35 g, 0.114 mol) in dry tetrahydrofuran (THF) (20 mL) cooled to 0° C. was added dropwise 2-thiophenesulfonyl chloride (5.0 g, 27.4 mmol). After the addition was completed, the reaction mixture was warmed to ambient temperature and stirred overnight. The mixture was extracted with ethyl acetate (3×80 mL) and the combined extracts were washed with water, dried over molecular sieves and concentrated. The residue was chromatographed on silica, eluting with 25% ethyl acetate-hexane, to yield 5.62 g (94%) of solid: mp 80°-82° C.

Workup

  1. additionAfter the addition
  2. extractionThe mixture was extracted with ethyl acetate (3×80 mL)
  3. washthe combined extracts were washed with water
  4. customdried over molecular sieves
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica
  7. washeluting with 25% ethyl acetate-hexane

Sources & evidence

ORD record
ord-a044f5eecb4c4b54a7b935c955dd6c4e
Source dataset
uspto-grants-1992_10
Patent number
US05153192

Reaction notes

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