Tert-Butylamine → 2-(4-Nitro-phenyl)-ethanesulfonic acid tert-butylamide

HRID 1711288Notes

Reaction equation

HRID 1711288 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][S:17](Cl)(=[O:19])=[O:18])=[CH:11][CH:10]=1)([O-:8])=[O:7]>C1COCC1>[C:1]([NH:5][S:17]([CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([N+:6]([O-:8])=[O:7])=[CH:10][CH:11]=1)(=[O:18])=[O:19])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 27611752-(4-nitrophenyl)ethanesulfonyl Chloride

Product 1

HCID 685055592-(4-Nitro-phenyl)-ethanesulfonic acid tert-butylamideYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-BuNH2 (15.6 mL, 148 mmol) in THF (50 mL) at 0° C., 2-(4-nitro-phenyl)-ethanesulfonyl chloride (WO 2006010079, 1.9 g, 7.6 mmol) was added portionwise. The resulting mixture was stirred for 24 h at RT. The solvent was removed in vacuo and the residue was taken up in DCM (50 mL) and cold 0.5 N HCl (50 mL). The organic layer was separated, dried (Na2SO4) and concentrated to obtain 2-(4-nitro-phenyl)-ethanesulfonic acid tert-butylamide (1.3 g, 62%) which was used directly without further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-104fb777ceed4c918a161632e419da38
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

Loading…