4-Nitrobenzenesulfonyl chloride → N-butyl-4-nitrobenzenesulfonamide

HRID 1814634Notes

Reaction equation

HRID 1814634 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:14]([NH2:18])[CH2:15][CH2:16][CH3:17]>C1COCC1.CN(C)C1C=CN=CC=1>[CH2:14]([NH:18][S:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:12])=[O:11])[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 2

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8007Butylamine

Product 1

HCID 1577957N-butyl-4-nitrobenzenesulfonamideYield 86.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Nitrophenylsulfonyl chloride (3.0 g, 13.5 mmol) was dissolved in THF and a catalytic amount of 4-dimethylaminopyridine and 1-butylamine (4.0 mL, 41 mmol) was added and the mixture was refluxed for 16 hours. The mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (100 mL) and washed with water (50 mL) and a 10% aqueous solution of sodium hydrogen carbonate (50 mL). The organic phase was dried (MgSO4) and concentrated in vacuo to afford 3.01 g (86%) of N-butyl-4-nitrobenzenesulfonamide as a solid.

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  4. washwashed with water (50 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-466c8dbeca8543299f6edcdb762eee65
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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