4-Nitrobenzenesulfonyl chloride → N-benzyl-4-nitrobenzenesulfonamide

HRID 497309Notes

Reaction equation

HRID 497309 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]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:14]([NH:21][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])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 7504BenzylamineHCID 8471Triethylamine

Product 1

HCID 745343N-benzyl-4-nitrobenzenesulfonamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of p-Nitrobenzenesulfonylchloride (274 g, 1.2 eq) in DCM (1 l), was added to a solution of benzylamine (500 g, 1 eq) and triethylamine (469 ml, 1.5 eq) in DCM (1 l) at 4° C. in small portions and then stirred for 1 h. Afterwards the mixture was stirred at rt for 16 h. The solvent was removed in vacuo and the residue was washed with a mixture of DCM/PE (1/1) at 4° C., filtered and dried in vacuo to give N-Benzyl-4-nitrobenzenesulfonamide. Yield 90%.

Workup

  1. stirringAfterwards the mixture was stirred at rt for 16 h
  2. customThe solvent was removed in vacuo
  3. washthe residue was washed with a mixture of DCM/PE (1/1) at 4° C.
  4. filtrationfiltered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-6d42ccb11e034bd2b12f3179fd4d5401
Source dataset
uspto-grants-2005_09
Patent number
US06949567B2

Reaction notes

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