Tert-Butylamine → N-tert-butyl-5-chloro-2-fluorobenzenesulfonamide

HRID 42361Notes

Reaction equation

HRID 42361 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.[C:13]([NH2:17])([CH3:16])([CH3:15])[CH3:14]>O1CCCC1>[C:13]([NH:17][S:8]([C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[F:12])(=[O:10])=[O:9])([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 27782735-Chloro-2-fluorobenzenesulfonyl chloride

Product 1

HCID 58275531N-tert-butyl-5-chloro-2-fluorobenzenesulfonamideYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-chloro-2-fluorobenzene-1-sulfonyl chloride (2.0 g) in tetrahydrofuran (30 ml) was added to a solution of tert-butylamine (9.15 ml) in tetrahydrofuran (70 ml) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The precipitate was removed by filtration and the filtrate was concentrated in vacuo to give N-tert-butyl-5-chloro-2-fluoro-benzenesulfonamide (2.2 g, 95% yield) as a white solid.

Workup

  1. customThe precipitate was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7e9f12671677409386781be71975540f
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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