Hydrochloric Acid → Benzenesulfonamide, 3-nitro-N-phenyl-

HRID 726924Notes

Reaction equation

HRID 726924 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(N(CC)CC)C.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl>ClCCl.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chloride

Product 1

HCID 120051Benzenesulfonamide, 3-nitro-N-phenyl-Yield 43.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-nitrobenzenesulfonyl chloride (3.08 g, 13.9 mmol) in 28 mL of dichloromethane was added triethylamine (3.88 mL, 27.8 mmol) and aniline (1.39 mL. 15.3 mmol). After 16 hours, the reaction was poured into ethyl acetate and 10% HCl solution, then washed with brine, dried (MgSO4) and concentrated in vacuo to provide the crude product. Purification by chromatography on silica gel (25-50% CH2Cl2 /hexane, then 5% MeOH/CH2Cl2) provided 1.68 g of the desired product as an off-white solid.

Workup

  1. washwashed with brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto provide the crude product
  5. customPurification by chromatography on silica gel (25-50% CH2Cl2 /hexane

Sources & evidence

ORD record
ord-400582e6f1b94987a7d65bb14fd5d3c9
Source dataset
uspto-grants-1998_01
Patent number
US05710171

Reaction notes

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