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

HRID 1633908Notes

Reaction equation

HRID 1633908 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-e78b9de2f3d84ac39232b87cce4149eb
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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