Isopropylamine → N-isopropyl-2-nitrobenzenesulfonamide

HRID 1887709Notes

Reaction equation

HRID 1887709 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[CH:14]([NH2:17])([CH3:16])[CH3:15].CCN(CC)CC>CO>[CH:14]([NH:17][S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 4154456N-isopropyl-2-nitrobenzenesulfonamideYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 2-nitrobenzene-1-sulfonyl chloride (1.11 g, 5.0 mmol) in MeOH (30 mL) was added isopropylamine (0.85 mL, 2.0 eq) and Et3N (1.4 mL, 2.0 eq). The mixture was stirred overnight at room temperature. The solvent was removed and the crude was purified by silica gel chromatography to obtain the desired product N-isopropyl-2-nitrobenzenesulfonamide (0.774 g, isolated yield 63%).

Workup

  1. customThe solvent was removed
  2. customthe crude was purified by silica gel chromatography

Sources & evidence

ORD record
ord-29352af446574d9ab7712363069a2ad9
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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